Route overview: Chicago to Honolulu (HNL) flight deals

Chicago (MDW) to Honolulu (HNL), Jul 21, 2027: round trips from $810, one way from $425

Chicago (MDW) to Honolulu (HNL), Jul 21, 2027: round trips from $810, one way from $425 on Axel, checked Nov 15, 2026. Lowest published fares: $810 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jul 21–22, 2027; $425 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jul 21, 2027; 1 adult, economy, checked Nov 15, 2026.

MDW → HNL1 adulteconomyOne way and round trips

34 flight options · 2 airlines

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One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

July 2027

Jul 21, 2027 · One waySouthwest AirlinesUp to 1 stop each way$425

Jul 21, 2027 · One wayDelta Air LinesUp to 1 stop each way$470

Jul 21, 2027 – Jul 22, 2027 · 1 nightSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 22, 2027 · 1 nightDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–22, 2027 · 1 night · 2 adults, 1 room): 3★ Stay Hotel Waikiki $164 a night · 4★ Hotel La Croix $218 a night · 5★ Alohilani Resort Waikiki Beach $282 a night

Jul 21, 2027 – Jul 23, 2027 · 2 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 23, 2027 · 2 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–23, 2027 · 2 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki $165 a night, $330 for 2 nights · 4★ Hotel La Croix $217 a night, $433 for 2 nights · 5★ Alohilani Resort Waikiki Beach $280 a night, $560 for 2 nights

Jul 21, 2027 – Jul 24, 2027 · 3 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 24, 2027 · 3 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki $170 a night, $509 for 3 nights · 4★ Hotel La Croix $219 a night, $658 for 3 nights · 5★ Alohilani Resort Waikiki Beach $288 a night, $865 for 3 nights

Jul 21, 2027 – Jul 25, 2027 · 4 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 25, 2027 · 4 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–25, 2027 · 4 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki $174 a night, $694 for 4 nights · 4★ Hotel La Croix $219 a night, $877 for 4 nights · 5★ Alohilani Resort Waikiki Beach $291 a night, $1,165 for 4 nights

Jul 21, 2027 – Jul 26, 2027 · 5 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 26, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–26, 2027 · 5 nights · 2 adults, 1 room): 3★ The Equus $166 a night, $828 for 5 nights · 4★ Hotel La Croix $220 a night, $1,100 for 5 nights · 5★ Alohilani Resort Waikiki Beach $291 a night, $1,456 for 5 nights

Jul 21, 2027 – Jul 27, 2027 · 6 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 27, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–27, 2027 · 6 nights · 2 adults, 1 room): 3★ The Equus $162 a night, $974 for 6 nights · 4★ Hotel La Croix $221 a night, $1,323 for 6 nights · 5★ Alohilani Resort Waikiki Beach $289 a night, $1,734 for 6 nights

Jul 21, 2027 – Jul 28, 2027 · 7 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 28, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–28, 2027 · 7 nights · 2 adults, 1 room): 3★ The Equus $157 a night, $1,101 for 7 nights · 4★ Hotel La Croix $222 a night, $1,554 for 7 nights · 5★ Alohilani Resort Waikiki Beach $288 a night, $2,013 for 7 nights

Jul 21, 2027 – Jul 29, 2027 · 8 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 29, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–29, 2027 · 8 nights · 2 adults, 1 room): 3★ The Equus $160 a night, $1,277 for 8 nights · 4★ Hotel La Croix $224 a night, $1,788 for 8 nights · 5★ Alohilani Resort Waikiki Beach $286 a night, $2,284 for 8 nights

Jul 21, 2027 – Jul 30, 2027 · 9 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 30, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–30, 2027 · 9 nights · 2 adults, 1 room): 3★ The Equus $161 a night, $1,453 for 9 nights · 4★ Hotel La Croix $224 a night, $2,015 for 9 nights · 5★ Alohilani Resort Waikiki Beach $285 a night, $2,568 for 9 nights

Jul 21, 2027 – Jul 31, 2027 · 10 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Jul 31, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21–31, 2027 · 10 nights · 2 adults, 1 room): 3★ The Equus $163 a night, $1,629 for 10 nights · 4★ Sheraton Princess Kaiulani Waikiki Beach $225 a night, $2,245 for 10 nights · 5★ Alohilani Resort Waikiki Beach $288 a night, $2,878 for 10 nights

Jul 21, 2027 – Aug 1, 2027 · 11 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Aug 1, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21 – Aug 1, 2027 · 11 nights · 2 adults, 1 room): 3★ The Equus $164 a night, $1,805 for 11 nights · 4★ Sheraton Princess Kaiulani Waikiki Beach $225 a night, $2,475 for 11 nights · 5★ Alohilani Resort Waikiki Beach $289 a night, $3,176 for 11 nights

Jul 21, 2027 – Aug 2, 2027 · 12 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Aug 2, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21 – Aug 2, 2027 · 12 nights · 2 adults, 1 room): 3★ The Equus $164 a night, $1,972 for 12 nights · 4★ Hotel La Croix $225 a night, $2,694 for 12 nights · 5★ Alohilani Resort Waikiki Beach $289 a night, $3,462 for 12 nights

Jul 21, 2027 – Aug 3, 2027 · 13 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Aug 3, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21 – Aug 3, 2027 · 13 nights · 2 adults, 1 room): 3★ The Equus $162 a night, $2,101 for 13 nights · 4★ Hotel La Croix $223 a night, $2,901 for 13 nights · 5★ Alohilani Resort Waikiki Beach $288 a night, $3,748 for 13 nights

Jul 21, 2027 – Aug 4, 2027 · 14 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Aug 4, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21 – Aug 4, 2027 · 14 nights · 2 adults, 1 room): 3★ The Equus $163 a night, $2,277 for 14 nights · 4★ Hotel La Croix $223 a night, $3,119 for 14 nights · 5★ Alohilani Resort Waikiki Beach $287 a night, $4,022 for 14 nights

Jul 21, 2027 – Aug 11, 2027 · 21 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Aug 11, 2027 · 21 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21 – Aug 11, 2027 · 21 nights · 2 adults, 1 room): 3★ The Equus · 4★ Aulani, A Disney Resort & Spa · 5★ Aulani, Disney Vacation Club Villas

Jul 21, 2027 – Aug 18, 2027 · 28 nightsSouthwest AirlinesUp to 1 stop each way$810

Jul 21, 2027 – Aug 18, 2027 · 28 nightsDelta Air LinesUp to 1 stop each way$890

Hotels for these nights (Jul 21 – Aug 18, 2027 · 28 nights · 2 adults, 1 room): 3★ The Equus · 4★ Aulani, A Disney Resort & Spa · 5★ Aulani, Disney Vacation Club Villas

Flights for your trip

Wed, Jul 21 · One way
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Example one-way total $425 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 · One way
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Example one-way total $470 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Thu, Jul 22
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
3:15 pmHNL
10h 25m
ONT · 1h 10m
6:40 am+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Thu, Jul 22
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Fri, Jul 23
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
1:20 pmHNL
12h 25m
SMF · 3h 15m
6:45 am+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Fri, Jul 23
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Sun, Jul 25
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
9:00 pmHNL
11h 35m
PHX · 2h 20m
1:35 pm+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Sun, Jul 25
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Mon, Jul 26
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
9:00 pmHNL
11h 35m
PHX · 2h 20m
1:35 pm+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Mon, Jul 26
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Wed, Jul 28
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
1:20 pmHNL
12h 25m
SMF · 3h 15m
6:45 am+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Wed, Jul 28
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Thu, Jul 29
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
3:15 pmHNL
10h 25m
ONT · 1h 10m
6:40 am+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Thu, Jul 29
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Sat, Jul 31
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
3:15 pmHNL
10h 25m
ONT · 1h 10m
6:40 am+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Sat, Jul 31
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Sun, Aug 1
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
9:00 pmHNL
11h 35m
PHX · 2h 20m
1:35 pm+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Sun, Aug 1
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Tue, Aug 3
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
1:20 pmHNL
12h 25m
SMF · 3h 15m
6:45 am+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Tue, Aug 3
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Wed, Aug 4
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
1:20 pmHNL
12h 25m
SMF · 3h 15m
6:45 am+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Wed, Aug 4
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Wed, Aug 18
Southwest Airlines
10:00 amMDW
13h 45m
OAK · 3h 35m
6:45 pmHNL
Southwest Airlines
1:20 pmHNL
12h 25m
SMF · 3h 15m
6:45 am+1MDW
Example round-trip total $810 · 1 adult · Taxes included
Search these dates
Wed, Jul 21 – Wed, Aug 18
Delta Air Lines
6:00 amMDW
16h 2m
ATL · 3h 56m
5:02 pmHNL
Delta Air Lines
4:25 pmHNL
13h 21m
DTW · 3h 10m
10:46 am+1MDW
Example round-trip total $890 · 1 adult · Taxes included
Search these dates

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Explore this route

All dates for this route Jul 20, 2027 · Return options Jul 22, 2027 · Return options Hotels in Honolulu with Axel

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Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Exact travel dates	Airline	Flights	Times, duration, stops	Total price	Price checked
2027-07-21 · one way	Southwest Airlines	WN3174 + WN808	10:00:00→18:45:00 13h 45m 1 stop via OAK	Axel-exclusive $425	Nov 15, 2026
2027-07-21 · one way	Delta Air Lines	DL1285 + DL438	06:00:00→17:02:00 16h 02m 1 stop via ATL	Axel-exclusive $470	Nov 15, 2026
2027-07-21 → 2027-07-22	Southwest Airlines	WN3174 + WN808 / WN2038 + WN3310	10:00:00→18:45:00 13h 45m 1 stop via OAK · 15:15:00→06:40:00 10h 25m 1 stop via ONT	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-22	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-07-23	Southwest Airlines	WN3174 + WN808 / WN4415 + WN4028	10:00:00→18:45:00 13h 45m 1 stop via OAK · 13:20:00→06:45:00 12h 25m 1 stop via SMF	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-23	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-07-24	Southwest Airlines	WN3174 + WN808 / WN2038 + WN3310	10:00:00→18:45:00 13h 45m 1 stop via OAK · 15:15:00→06:40:00 10h 25m 1 stop via ONT	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-24	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-07-25	Southwest Airlines	WN3174 + WN808 / WN1276 + WN3443	10:00:00→18:45:00 13h 45m 1 stop via OAK · 21:00:00→13:35:00 11h 35m 1 stop via PHX	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-25	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-07-26	Southwest Airlines	WN3174 + WN808 / WN1276 + WN3443	10:00:00→18:45:00 13h 45m 1 stop via OAK · 21:00:00→13:35:00 11h 35m 1 stop via PHX	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-26	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-07-27	Southwest Airlines	WN3174 + WN808 / WN4415 + WN4028	10:00:00→18:45:00 13h 45m 1 stop via OAK · 13:20:00→06:45:00 12h 25m 1 stop via SMF	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-27	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-07-28	Southwest Airlines	WN3174 + WN808 / WN4415 + WN4028	10:00:00→18:45:00 13h 45m 1 stop via OAK · 13:20:00→06:45:00 12h 25m 1 stop via SMF	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-28	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-07-29	Southwest Airlines	WN3174 + WN808 / WN2038 + WN3310	10:00:00→18:45:00 13h 45m 1 stop via OAK · 15:15:00→06:40:00 10h 25m 1 stop via ONT	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-29	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-07-30	Southwest Airlines	WN3174 + WN808 / WN4415 + WN4028	10:00:00→18:45:00 13h 45m 1 stop via OAK · 13:20:00→06:45:00 12h 25m 1 stop via SMF	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-30	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-07-31	Southwest Airlines	WN3174 + WN808 / WN2038 + WN3310	10:00:00→18:45:00 13h 45m 1 stop via OAK · 15:15:00→06:40:00 10h 25m 1 stop via ONT	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-07-31	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-08-01	Southwest Airlines	WN3174 + WN808 / WN1276 + WN3443	10:00:00→18:45:00 13h 45m 1 stop via OAK · 21:00:00→13:35:00 11h 35m 1 stop via PHX	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-08-01	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-08-02	Southwest Airlines	WN3174 + WN808 / WN1276 + WN3443	10:00:00→18:45:00 13h 45m 1 stop via OAK · 21:00:00→13:35:00 11h 35m 1 stop via PHX	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-08-02	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-08-03	Southwest Airlines	WN3174 + WN808 / WN4415 + WN4028	10:00:00→18:45:00 13h 45m 1 stop via OAK · 13:20:00→06:45:00 12h 25m 1 stop via SMF	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-08-03	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-08-04	Southwest Airlines	WN3174 + WN808 / WN4415 + WN4028	10:00:00→18:45:00 13h 45m 1 stop via OAK · 13:20:00→06:45:00 12h 25m 1 stop via SMF	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-08-04	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-08-11	Southwest Airlines	WN3174 + WN808 / WN4415 + WN4028	10:00:00→18:45:00 13h 45m 1 stop via OAK · 13:20:00→06:45:00 12h 25m 1 stop via SMF	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-08-11	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026
2027-07-21 → 2027-08-18	Southwest Airlines	WN3174 + WN808 / WN4415 + WN4028	10:00:00→18:45:00 13h 45m 1 stop via OAK · 13:20:00→06:45:00 12h 25m 1 stop via SMF	Axel-exclusive $810	Nov 15, 2026
2027-07-21 → 2027-08-18	Delta Air Lines	DL1285 + DL438 / DL386 + DL4684	06:00:00→17:02:00 16h 02m 1 stop via ATL · 16:25:00→10:46:00 13h 21m 1 stop via DTW	Axel-exclusive $890	Nov 15, 2026

Hotels in Honolulu for these trips

Hotels: under a trip, hotels in Honolulu for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

Hotels in Honolulu for these nights (Jul 21–22, 2027 · 1 night · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $164 a night · 4★ Hotel La Croix, $218 a night · 5★ Alohilani Resort Waikiki Beach, $282 a night
Hotels in Honolulu for these nights (Jul 21–23, 2027 · 2 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $165 a night, $330 for 2 nights · 4★ Hotel La Croix, $217 a night, $433 for 2 nights · 5★ Alohilani Resort Waikiki Beach, $280 a night, $560 for 2 nights
Hotels in Honolulu for these nights (Jul 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $170 a night, $509 for 3 nights · 4★ Hotel La Croix, $219 a night, $658 for 3 nights · 5★ Alohilani Resort Waikiki Beach, $288 a night, $865 for 3 nights
Hotels in Honolulu for these nights (Jul 21–25, 2027 · 4 nights · 2 adults, 1 room): 3★ Stay Hotel Waikiki, $174 a night, $694 for 4 nights · 4★ Hotel La Croix, $219 a night, $877 for 4 nights · 5★ Alohilani Resort Waikiki Beach, $291 a night, $1,165 for 4 nights
Hotels in Honolulu for these nights (Jul 21–26, 2027 · 5 nights · 2 adults, 1 room): 3★ The Equus, $166 a night, $828 for 5 nights · 4★ Hotel La Croix, $220 a night, $1,100 for 5 nights · 5★ Alohilani Resort Waikiki Beach, $291 a night, $1,456 for 5 nights
Hotels in Honolulu for these nights (Jul 21–27, 2027 · 6 nights · 2 adults, 1 room): 3★ The Equus, $162 a night, $974 for 6 nights · 4★ Hotel La Croix, $221 a night, $1,323 for 6 nights · 5★ Alohilani Resort Waikiki Beach, $289 a night, $1,734 for 6 nights
Hotels in Honolulu for these nights (Jul 21–28, 2027 · 7 nights · 2 adults, 1 room): 3★ The Equus, $157 a night, $1,101 for 7 nights · 4★ Hotel La Croix, $222 a night, $1,554 for 7 nights · 5★ Alohilani Resort Waikiki Beach, $288 a night, $2,013 for 7 nights
Hotels in Honolulu for these nights (Jul 21–29, 2027 · 8 nights · 2 adults, 1 room): 3★ The Equus, $160 a night, $1,277 for 8 nights · 4★ Hotel La Croix, $224 a night, $1,788 for 8 nights · 5★ Alohilani Resort Waikiki Beach, $286 a night, $2,284 for 8 nights
Hotels in Honolulu for these nights (Jul 21–30, 2027 · 9 nights · 2 adults, 1 room): 3★ The Equus, $161 a night, $1,453 for 9 nights · 4★ Hotel La Croix, $224 a night, $2,015 for 9 nights · 5★ Alohilani Resort Waikiki Beach, $285 a night, $2,568 for 9 nights
Hotels in Honolulu for these nights (Jul 21–31, 2027 · 10 nights · 2 adults, 1 room): 3★ The Equus, $163 a night, $1,629 for 10 nights · 4★ Sheraton Princess Kaiulani Waikiki Beach, $225 a night, $2,245 for 10 nights · 5★ Alohilani Resort Waikiki Beach, $288 a night, $2,878 for 10 nights
Hotels in Honolulu for these nights (Jul 21 – Aug 1, 2027 · 11 nights · 2 adults, 1 room): 3★ The Equus, $164 a night, $1,805 for 11 nights · 4★ Sheraton Princess Kaiulani Waikiki Beach, $225 a night, $2,475 for 11 nights · 5★ Alohilani Resort Waikiki Beach, $289 a night, $3,176 for 11 nights
Hotels in Honolulu for these nights (Jul 21 – Aug 2, 2027 · 12 nights · 2 adults, 1 room): 3★ The Equus, $164 a night, $1,972 for 12 nights · 4★ Hotel La Croix, $225 a night, $2,694 for 12 nights · 5★ Alohilani Resort Waikiki Beach, $289 a night, $3,462 for 12 nights
Hotels in Honolulu for these nights (Jul 21 – Aug 3, 2027 · 13 nights · 2 adults, 1 room): 3★ The Equus, $162 a night, $2,101 for 13 nights · 4★ Hotel La Croix, $223 a night, $2,901 for 13 nights · 5★ Alohilani Resort Waikiki Beach, $288 a night, $3,748 for 13 nights
Hotels in Honolulu for these nights (Jul 21 – Aug 4, 2027 · 14 nights · 2 adults, 1 room): 3★ The Equus, $163 a night, $2,277 for 14 nights · 4★ Hotel La Croix, $223 a night, $3,119 for 14 nights · 5★ Alohilani Resort Waikiki Beach, $287 a night, $4,022 for 14 nights
Hotels in Honolulu for these nights (Jul 21 – Aug 11, 2027 · 21 nights · 2 adults, 1 room): 3★ The Equus · 4★ Aulani, A Disney Resort & Spa · 5★ Aulani, Disney Vacation Club Villas
Hotels in Honolulu for these nights (Jul 21 – Aug 18, 2027 · 28 nights · 2 adults, 1 room): 3★ The Equus · 4★ Aulani, A Disney Resort & Spa · 5★ Aulani, Disney Vacation Club Villas

All hotels in Honolulu

Route overview: Chicago to Honolulu (HNL) flight deals

2027-07-21 · one way · Axel-exclusive $425

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.

2027-07-21 · one way · Axel-exclusive $470

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.

2027-07-21 → 2027-07-22 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN2038 / WN3310: HNL 2027-07-22 15:15:00 → MDW 2027-07-23 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
- WN2038: HNL 2027-07-22 15:15:00 → ONT 2027-07-22 23:45:00; layover at ONT: 70 minutes.
- WN3310: ONT 2027-07-23 00:55:00 → MDW 2027-07-23 06:40:00.

2027-07-21 → 2027-07-22 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-07-22 16:25:00 → MDW 2027-07-23 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-07-22 16:25:00 → DTW 2027-07-23 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-07-23 10:10:00 → MDW 2027-07-23 10:46:00.

2027-07-21 → 2027-07-23 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN4415 / WN4028: HNL 2027-07-23 13:20:00 → MDW 2027-07-24 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
- WN4415: HNL 2027-07-23 13:20:00 → SMF 2027-07-23 21:40:00; layover at SMF: 195 minutes.
- WN4028: SMF 2027-07-24 00:55:00 → MDW 2027-07-24 06:45:00.

2027-07-21 → 2027-07-23 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-07-23 16:25:00 → MDW 2027-07-24 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-07-23 16:25:00 → DTW 2027-07-24 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-07-24 10:10:00 → MDW 2027-07-24 10:46:00.

2027-07-21 → 2027-07-25 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN1276 / WN3443: HNL 2027-07-25 21:00:00 → MDW 2027-07-26 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
- WN1276: HNL 2027-07-25 21:00:00 → PHX 2027-07-26 06:00:00; layover at PHX: 140 minutes.
- WN3443: PHX 2027-07-26 08:20:00 → MDW 2027-07-26 13:35:00.

2027-07-21 → 2027-07-25 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-07-25 16:25:00 → MDW 2027-07-26 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-07-25 16:25:00 → DTW 2027-07-26 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-07-26 10:10:00 → MDW 2027-07-26 10:46:00.

2027-07-21 → 2027-07-26 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN1276 / WN3443: HNL 2027-07-26 21:00:00 → MDW 2027-07-27 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
- WN1276: HNL 2027-07-26 21:00:00 → PHX 2027-07-27 06:00:00; layover at PHX: 140 minutes.
- WN3443: PHX 2027-07-27 08:20:00 → MDW 2027-07-27 13:35:00.

2027-07-21 → 2027-07-26 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-07-26 16:25:00 → MDW 2027-07-27 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-07-26 16:25:00 → DTW 2027-07-27 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-07-27 10:10:00 → MDW 2027-07-27 10:46:00.

2027-07-21 → 2027-07-28 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN4415 / WN4028: HNL 2027-07-28 13:20:00 → MDW 2027-07-29 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
- WN4415: HNL 2027-07-28 13:20:00 → SMF 2027-07-28 21:40:00; layover at SMF: 195 minutes.
- WN4028: SMF 2027-07-29 00:55:00 → MDW 2027-07-29 06:45:00.

2027-07-21 → 2027-07-28 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-07-28 16:25:00 → MDW 2027-07-29 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-07-28 16:25:00 → DTW 2027-07-29 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-07-29 10:10:00 → MDW 2027-07-29 10:46:00.

2027-07-21 → 2027-07-29 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN2038 / WN3310: HNL 2027-07-29 15:15:00 → MDW 2027-07-30 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
- WN2038: HNL 2027-07-29 15:15:00 → ONT 2027-07-29 23:45:00; layover at ONT: 70 minutes.
- WN3310: ONT 2027-07-30 00:55:00 → MDW 2027-07-30 06:40:00.

2027-07-21 → 2027-07-29 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-07-29 16:25:00 → MDW 2027-07-30 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-07-29 16:25:00 → DTW 2027-07-30 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-07-30 10:10:00 → MDW 2027-07-30 10:46:00.

2027-07-21 → 2027-07-31 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN2038 / WN3310: HNL 2027-07-31 15:15:00 → MDW 2027-08-01 06:40:00; 1 stop(s) via ONT; 625 minutes. Local airport times.
- WN2038: HNL 2027-07-31 15:15:00 → ONT 2027-07-31 23:45:00; layover at ONT: 70 minutes.
- WN3310: ONT 2027-08-01 00:55:00 → MDW 2027-08-01 06:40:00.

2027-07-21 → 2027-07-31 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-07-31 16:25:00 → MDW 2027-08-01 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-07-31 16:25:00 → DTW 2027-08-01 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-08-01 10:10:00 → MDW 2027-08-01 10:46:00.

2027-07-21 → 2027-08-01 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN1276 / WN3443: HNL 2027-08-01 21:00:00 → MDW 2027-08-02 13:35:00; 1 stop(s) via PHX; 695 minutes. Local airport times.
- WN1276: HNL 2027-08-01 21:00:00 → PHX 2027-08-02 06:00:00; layover at PHX: 140 minutes.
- WN3443: PHX 2027-08-02 08:20:00 → MDW 2027-08-02 13:35:00.

2027-07-21 → 2027-08-01 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-08-01 16:25:00 → MDW 2027-08-02 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-08-01 16:25:00 → DTW 2027-08-02 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-08-02 10:10:00 → MDW 2027-08-02 10:46:00.

2027-07-21 → 2027-08-03 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN4415 / WN4028: HNL 2027-08-03 13:20:00 → MDW 2027-08-04 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
- WN4415: HNL 2027-08-03 13:20:00 → SMF 2027-08-03 21:40:00; layover at SMF: 195 minutes.
- WN4028: SMF 2027-08-04 00:55:00 → MDW 2027-08-04 06:45:00.

2027-07-21 → 2027-08-03 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-08-03 16:25:00 → MDW 2027-08-04 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-08-03 16:25:00 → DTW 2027-08-04 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-08-04 10:10:00 → MDW 2027-08-04 10:46:00.

2027-07-21 → 2027-08-04 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN4415 / WN4028: HNL 2027-08-04 13:20:00 → MDW 2027-08-05 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
- WN4415: HNL 2027-08-04 13:20:00 → SMF 2027-08-04 21:40:00; layover at SMF: 195 minutes.
- WN4028: SMF 2027-08-05 00:55:00 → MDW 2027-08-05 06:45:00.

2027-07-21 → 2027-08-04 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-08-04 16:25:00 → MDW 2027-08-05 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-08-04 16:25:00 → DTW 2027-08-05 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-08-05 10:10:00 → MDW 2027-08-05 10:46:00.

2027-07-21 → 2027-08-18 · Axel-exclusive $810

Southwest Airlines WN3174 / WN808: MDW 2027-07-21 10:00:00 → HNL 2027-07-21 18:45:00; 1 stop(s) via OAK; 825 minutes. Local airport times.
- WN3174: MDW 2027-07-21 10:00:00 → OAK 2027-07-21 12:40:00; layover at OAK: 215 minutes.
- WN808: OAK 2027-07-21 16:15:00 → HNL 2027-07-21 18:45:00.
Southwest Airlines WN4415 / WN4028: HNL 2027-08-18 13:20:00 → MDW 2027-08-19 06:45:00; 1 stop(s) via SMF; 745 minutes. Local airport times.
- WN4415: HNL 2027-08-18 13:20:00 → SMF 2027-08-18 21:40:00; layover at SMF: 195 minutes.
- WN4028: SMF 2027-08-19 00:55:00 → MDW 2027-08-19 06:45:00.

2027-07-21 → 2027-08-18 · Axel-exclusive $890

Delta Air Lines DL1285 / DL438: MDW 2027-07-21 06:00:00 → HNL 2027-07-21 17:02:00; 1 stop(s) via ATL; 962 minutes. Local airport times.
- DL1285: MDW 2027-07-21 06:00:00 → ATL 2027-07-21 09:03:00; layover at ATL: 236 minutes.
- DL438: ATL 2027-07-21 12:59:00 → HNL 2027-07-21 17:02:00.
Delta Air Lines DL386 / DL4684: HNL 2027-08-18 16:25:00 → MDW 2027-08-19 10:46:00; 1 stop(s) via DTW; 801 minutes. Local airport times.
- DL386: HNL 2027-08-18 16:25:00 → DTW 2027-08-19 07:00:00; layover at DTW: 190 minutes.
- DL4684: DTW 2027-08-19 10:10:00 → MDW 2027-08-19 10:46:00.

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This page: Chicago (MDW) to Honolulu (HNL) · Jul 21, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Honolulu for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
Next: each row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Chicago to Honolulu (HNL) flight deals · Flight search guide.
Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.