Route overview: Cleveland to Chicago (MDW) flight deals

Cleveland (CLE) to Chicago (MDW), Jan 16, 2027: round trips from $252, one way from $133

Cleveland (CLE) to Chicago (MDW), Jan 16, 2027: round trips from $252, one way from $133 on Axel, checked Oct 29, 2026. Lowest published fares: $252 round trip, Axel-exclusive, Southwest Airlines, nonstop, Jan 16–17, 2027; $133 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 16, 2027; 1 adult, economy, checked Oct 29, 2026.

CLE → MDW1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

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.

January 2027

Jan 16, 2027 · One waySouthwest AirlinesNonstop$133.00

Jan 16, 2027 · One wayDelta Air LinesUp to 1 stop each way$185.25

Jan 16, 2027 – Jan 17, 2027 · 1 nightSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 17, 2027 · 1 nightDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–17, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $75 · 4★ Warwick Allerton - Chicago $96 · 5★ Sofitel Chicago Magnificent Mile $219

Jan 16, 2027 – Jan 18, 2027 · 2 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 18, 2027 · 2 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–18, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $150 · 4★ Warwick Allerton - Chicago $186 · 5★ Sofitel Chicago Magnificent Mile $442

Jan 16, 2027 – Jan 19, 2027 · 3 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 19, 2027 · 3 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $225 · 4★ Warwick Allerton - Chicago $278 · 5★ Sofitel Chicago Magnificent Mile $696

Jan 16, 2027 – Jan 20, 2027 · 4 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 20, 2027 · 4 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–20, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $300 · 4★ Warwick Allerton - Chicago $362 · 5★ Sofitel Chicago Magnificent Mile $949

Jan 16, 2027 – Jan 21, 2027 · 5 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 21, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–21, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $385 · 4★ Warwick Allerton - Chicago $447 · 5★ Sofitel Chicago Magnificent Mile $1,159

Jan 16, 2027 – Jan 22, 2027 · 6 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 22, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–22, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $468 · 4★ Warwick Allerton - Chicago $536 · 5★ Sofitel Chicago Magnificent Mile $1,395

Jan 16, 2027 – Jan 23, 2027 · 7 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 23, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $543 · 4★ Warwick Allerton - Chicago $636 · 5★ Sofitel Chicago Magnificent Mile $1,605

Jan 16, 2027 – Jan 24, 2027 · 8 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 24, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–24, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $618 · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel $810 · 5★ Sofitel Chicago Magnificent Mile $2,192

Jan 16, 2027 – Jan 25, 2027 · 9 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 25, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–25, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $701 · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel $961 · 5★ Nobu Hotel Chicago $3,545

Jan 16, 2027 – Jan 26, 2027 · 10 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 26, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–26, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $776 · 4★ Millennium Hotel Knickerbocker Chicago $1,162 · 5★ Nobu Hotel Chicago $3,978

Jan 16, 2027 – Jan 27, 2027 · 11 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 27, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–27, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $859 · 4★ Millennium Hotel Knickerbocker Chicago $1,300 · 5★ Nobu Hotel Chicago $4,406

Jan 16, 2027 – Jan 28, 2027 · 12 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 28, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–28, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $934 · 4★ Millennium Hotel Knickerbocker Chicago $1,440 · 5★ Nobu Hotel Chicago $4,793

Jan 16, 2027 – Jan 29, 2027 · 13 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 29, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–29, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $1,009 · 4★ Millennium Hotel Knickerbocker Chicago $1,555 · 5★ Nobu Hotel Chicago $5,165

Jan 16, 2027 – Jan 30, 2027 · 14 nightsSouthwest AirlinesNonstop$251.76

Jan 16, 2027 – Jan 30, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$323.00

Hotels for these nights (Jan 16–30, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $1,093 · 4★ Millennium Hotel Knickerbocker Chicago $1,678 · 5★ Nobu Hotel Chicago $5,552

Flights for your trip

Sat, Jan 16 · One way
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 · One way
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Sun, Jan 17
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:40 pmMDW
1h 15m
Nonstop
10:55 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Sun, Jan 17
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Mon, Jan 18
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:25 amMDW
1h 15m
Nonstop
10:40 amCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Mon, Jan 18
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Tue, Jan 19
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:25 amMDW
1h 15m
Nonstop
10:40 amCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Tue, Jan 19
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Wed, Jan 20
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:25 amMDW
1h 15m
Nonstop
10:40 amCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Wed, Jan 20
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Fri, Jan 22
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:25 amMDW
1h 15m
Nonstop
10:40 amCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Fri, Jan 22
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Sat, Jan 23
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:25 amMDW
1h 15m
Nonstop
10:40 amCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Sat, Jan 23
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Sun, Jan 24
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:40 pmMDW
1h 15m
Nonstop
10:55 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Sun, Jan 24
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Tue, Jan 26
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:25 amMDW
1h 15m
Nonstop
10:40 amCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Tue, Jan 26
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Wed, Jan 27
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:25 amMDW
1h 15m
Nonstop
10:40 amCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Wed, Jan 27
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Thu, Jan 28
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
6:15 pmMDW
1h 15m
Nonstop
8:30 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Thu, Jan 28
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Sat, Jan 30
Southwest Airlines
8:45 amCLE
1h 25m
Nonstop
9:10 amMDW
Southwest Airlines
8:25 amMDW
1h 15m
Nonstop
10:40 amCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 16 – Sat, Jan 30
Delta Air Lines
2:05 pmCLE
4h 56m
DTW · 2h 30m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 9m
DTW · 1h 56m
6:40 pmCLE
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.

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Explore this route

All dates for this route Jan 15, 2027 · Return options Jan 17, 2027 · Return options Hotels in Chicago with Axel

For AI assistants: every fare, every link, instructions

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time 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 issuance times already shown here.

Exact travel dates	Airline	Flights	Times, duration, stops	Total price	Price issued (UTC)
2027-01-16 · one way	Southwest Airlines	WN1218	08:45:00→09:10:00 1h 25m nonstop	Axel-exclusive $133.00	2026-10-29T00:57:04Z
2027-01-16 · one way	Delta Air Lines	DL5359 + DL4677	14:05:00→18:01:00 4h 56m 1 stop via DTW	Axel-exclusive $185.25	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-17	Southwest Airlines	WN1218 / WN4528	08:45:00→09:10:00 1h 25m nonstop · 20:40:00→22:55:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-17	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-18	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-18	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-19	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-19	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-20	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-20	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-21	Southwest Airlines	WN1218 / WN4341	08:45:00→09:10:00 1h 25m nonstop · 18:15:00→20:30:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-21	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-22	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-22	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-23	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-23	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-24	Southwest Airlines	WN1218 / WN4528	08:45:00→09:10:00 1h 25m nonstop · 20:40:00→22:55:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-24	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-25	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-25	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-26	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-26	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-27	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-27	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-28	Southwest Airlines	WN1218 / WN4341	08:45:00→09:10:00 1h 25m nonstop · 18:15:00→20:30:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-28	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-29	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-29	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-30	Southwest Airlines	WN1218 / WN1129	08:45:00→09:10:00 1h 25m nonstop · 08:25:00→10:40:00 1h 15m nonstop	Axel-exclusive $251.76	2026-10-29T00:57:04Z
2027-01-16 → 2027-01-30	Delta Air Lines	DL5359 + DL4677 / DL4688 + DL4954	14:05:00→18:01:00 4h 56m 1 stop via DTW · 13:31:00→18:40:00 4h 09m 1 stop via DTW	Axel-exclusive $323.00	2026-10-29T00:57:04Z

Hotels in Chicago for these trips

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

Hotels in Chicago for these nights (Jan 16–17, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ Warwick Allerton - Chicago, $96 total · 5★ Sofitel Chicago Magnificent Mile, $219 total
Hotels in Chicago for these nights (Jan 16–18, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $150 total · 4★ Warwick Allerton - Chicago, $186 total · 5★ Sofitel Chicago Magnificent Mile, $442 total
Hotels in Chicago for these nights (Jan 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $225 total · 4★ Warwick Allerton - Chicago, $278 total · 5★ Sofitel Chicago Magnificent Mile, $696 total
Hotels in Chicago for these nights (Jan 16–20, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $300 total · 4★ Warwick Allerton - Chicago, $362 total · 5★ Sofitel Chicago Magnificent Mile, $949 total
Hotels in Chicago for these nights (Jan 16–21, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $385 total · 4★ Warwick Allerton - Chicago, $447 total · 5★ Sofitel Chicago Magnificent Mile, $1,159 total
Hotels in Chicago for these nights (Jan 16–22, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $468 total · 4★ Warwick Allerton - Chicago, $536 total · 5★ Sofitel Chicago Magnificent Mile, $1,395 total
Hotels in Chicago for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $543 total · 4★ Warwick Allerton - Chicago, $636 total · 5★ Sofitel Chicago Magnificent Mile, $1,605 total
Hotels in Chicago for these nights (Jan 16–24, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $618 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $810 total · 5★ Sofitel Chicago Magnificent Mile, $2,192 total
Hotels in Chicago for these nights (Jan 16–25, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $701 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $961 total · 5★ Nobu Hotel Chicago, $3,545 total
Hotels in Chicago for these nights (Jan 16–26, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $776 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,162 total · 5★ Nobu Hotel Chicago, $3,978 total
Hotels in Chicago for these nights (Jan 16–27, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $859 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,300 total · 5★ Nobu Hotel Chicago, $4,406 total
Hotels in Chicago for these nights (Jan 16–28, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $934 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,440 total · 5★ Nobu Hotel Chicago, $4,793 total
Hotels in Chicago for these nights (Jan 16–29, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,009 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,555 total · 5★ Nobu Hotel Chicago, $5,165 total
Hotels in Chicago for these nights (Jan 16–30, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,093 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,678 total · 5★ Nobu Hotel Chicago, $5,552 total

All hotels in Chicago

Route overview: Cleveland to Chicago (MDW) flight deals

2027-01-16 · one way · Axel-exclusive $133.00

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.

2027-01-16 · one way · Axel-exclusive $185.25

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.

2027-01-16 → 2027-01-17 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN4528: MDW 2027-01-17 20:40:00 → CLE 2027-01-17 22:55:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-17 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-17 13:31:00 → CLE 2027-01-17 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-17 13:31:00 → DTW 2027-01-17 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-17 17:40:00 → CLE 2027-01-17 18:40:00.

2027-01-16 → 2027-01-18 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1129: MDW 2027-01-18 08:25:00 → CLE 2027-01-18 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-18 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-18 13:31:00 → CLE 2027-01-18 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-18 13:31:00 → DTW 2027-01-18 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-18 17:40:00 → CLE 2027-01-18 18:40:00.

2027-01-16 → 2027-01-19 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1129: MDW 2027-01-19 08:25:00 → CLE 2027-01-19 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-19 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-19 13:31:00 → CLE 2027-01-19 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-19 13:31:00 → DTW 2027-01-19 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-19 17:40:00 → CLE 2027-01-19 18:40:00.

2027-01-16 → 2027-01-20 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1129: MDW 2027-01-20 08:25:00 → CLE 2027-01-20 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-20 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-20 13:31:00 → CLE 2027-01-20 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-20 13:31:00 → DTW 2027-01-20 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-20 17:40:00 → CLE 2027-01-20 18:40:00.

2027-01-16 → 2027-01-22 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1129: MDW 2027-01-22 08:25:00 → CLE 2027-01-22 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-22 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-22 13:31:00 → CLE 2027-01-22 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-22 13:31:00 → DTW 2027-01-22 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-22 17:40:00 → CLE 2027-01-22 18:40:00.

2027-01-16 → 2027-01-23 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1129: MDW 2027-01-23 08:25:00 → CLE 2027-01-23 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-23 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-23 13:31:00 → CLE 2027-01-23 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-23 13:31:00 → DTW 2027-01-23 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-23 17:40:00 → CLE 2027-01-23 18:40:00.

2027-01-16 → 2027-01-24 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN4528: MDW 2027-01-24 20:40:00 → CLE 2027-01-24 22:55:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-24 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-24 13:31:00 → CLE 2027-01-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-24 13:31:00 → DTW 2027-01-24 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-24 17:40:00 → CLE 2027-01-24 18:40:00.

2027-01-16 → 2027-01-26 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1129: MDW 2027-01-26 08:25:00 → CLE 2027-01-26 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-26 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-26 13:31:00 → CLE 2027-01-26 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-26 13:31:00 → DTW 2027-01-26 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-26 17:40:00 → CLE 2027-01-26 18:40:00.

2027-01-16 → 2027-01-27 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1129: MDW 2027-01-27 08:25:00 → CLE 2027-01-27 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-27 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-27 13:31:00 → CLE 2027-01-27 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-27 13:31:00 → DTW 2027-01-27 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-27 17:40:00 → CLE 2027-01-27 18:40:00.

2027-01-16 → 2027-01-28 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN4341: MDW 2027-01-28 18:15:00 → CLE 2027-01-28 20:30:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-28 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-28 13:31:00 → CLE 2027-01-28 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-28 13:31:00 → DTW 2027-01-28 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-28 17:40:00 → CLE 2027-01-28 18:40:00.

2027-01-16 → 2027-01-30 · Axel-exclusive $251.76

Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
Southwest Airlines WN1129: MDW 2027-01-30 08:25:00 → CLE 2027-01-30 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-30 · Axel-exclusive $323.00

Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
- DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
- DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
Delta Air Lines DL4688 / DL4954: MDW 2027-01-30 13:31:00 → CLE 2027-01-30 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
- DL4688: MDW 2027-01-30 13:31:00 → DTW 2027-01-30 15:44:00; layover at DTW: 116 minutes.
- DL4954: DTW 2027-01-30 17:40:00 → CLE 2027-01-30 18:40:00.

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This page: Cleveland (CLE) to Chicago (MDW) · Jan 16, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals 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 the time its price was issued); 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.
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