Route overview: San Antonio to Chicago (MDW) flight deals

San Antonio (SAT) to Chicago (MDW), Jan 11, 2027: round trips from $290, one way from $155

San Antonio (SAT) to Chicago (MDW), Jan 11, 2027: round trips from $290, one way from $155 on Axel, checked Oct 29, 2026. Lowest published fares: $290 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 11–14, 2027; $155 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jan 11, 2027; 1 adult, economy, checked Oct 29, 2026.

SAT → 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 11, 2027 · One waySouthwest AirlinesUp to 1 stop each way$155.00

Jan 11, 2027 · One wayDelta Air LinesUp to 1 stop each way$190.00

Jan 11, 2027 – Jan 12, 2027 · 1 nightSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 12, 2027 · 1 nightDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey $65 · 4★ Warwick Allerton - Chicago $85 · 5★ Sofitel Chicago Magnificent Mile $254

Jan 11, 2027 – Jan 13, 2027 · 2 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 13, 2027 · 2 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–13, 2027 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey $138 · 4★ Warwick Allerton - Chicago $172 · 5★ Sofitel Chicago Magnificent Mile $508

Jan 11, 2027 – Jan 14, 2027 · 3 nightsSouthwest AirlinesUp to 1 stop each way$290.00

Jan 11, 2027 – Jan 14, 2027 · 3 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey $212 · 4★ Warwick Allerton - Chicago $260 · 5★ Sofitel Chicago Magnificent Mile $762

Jan 11, 2027 – Jan 15, 2027 · 4 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 15, 2027 · 4 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–15, 2027 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey $286 · 4★ Warwick Allerton - Chicago $349 · 5★ Sofitel Chicago Magnificent Mile $976

Jan 11, 2027 – Jan 16, 2027 · 5 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 16, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–16, 2027 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey $390 · 4★ Warwick Allerton - Chicago $440 · 5★ Sofitel Chicago Magnificent Mile $1,191

Jan 11, 2027 – Jan 17, 2027 · 6 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 17, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–17, 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 $1,410

Jan 11, 2027 – Jan 18, 2027 · 7 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 18, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–18, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $543 · 4★ Warwick Allerton - Chicago $626 · 5★ Sofitel Chicago Magnificent Mile $1,633

Jan 11, 2027 – Jan 19, 2027 · 8 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 19, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–19, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $618 · 4★ Warwick Allerton - Chicago $718 · 5★ Sofitel Chicago Magnificent Mile $1,887

Jan 11, 2027 – Jan 20, 2027 · 9 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 20, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–20, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $693 · 4★ Warwick Allerton - Chicago $802 · 5★ Sofitel Chicago Magnificent Mile $2,140

Jan 11, 2027 – Jan 21, 2027 · 10 nightsSouthwest AirlinesUp to 1 stop each way$290.00

Jan 11, 2027 – Jan 21, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–21, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $778 · 4★ Warwick Allerton - Chicago $887 · 5★ Sofitel Chicago Magnificent Mile $2,350

Jan 11, 2027 – Jan 22, 2027 · 11 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 22, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–22, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $861 · 4★ Warwick Allerton - Chicago $976 · 5★ Sofitel Chicago Magnificent Mile $2,586

Jan 11, 2027 – Jan 23, 2027 · 12 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 23, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–23, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $936 · 4★ Warwick Allerton - Chicago $1,076 · 5★ Sofitel Chicago Magnificent Mile $2,796

Jan 11, 2027 – Jan 24, 2027 · 13 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 24, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–24, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $1,011 · 4★ Warwick Allerton - Chicago $1,266 · 5★ Sofitel Chicago Magnificent Mile $3,383

Jan 11, 2027 – Jan 25, 2027 · 14 nightsSouthwest AirlinesUp to 1 stop each way$300.00

Jan 11, 2027 – Jan 25, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$360.00

Hotels for these nights (Jan 11–25, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $1,094 · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel $1,469 · 5★ Nobu Hotel Chicago $5,484

Flights for your trip

Mon, Jan 11 · One way
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 · One way
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Tue, Jan 12
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
10:00 amMDW
2h 55m
Nonstop
12:55 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Tue, Jan 12
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Wed, Jan 13
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Wed, Jan 13
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Thu, Jan 14
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
11:30 amMDW
4h 55m
STL · 1h 25m
4:25 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Thu, Jan 14
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Fri, Jan 15
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Fri, Jan 15
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Sun, Jan 17
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Sun, Jan 17
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Mon, Jan 18
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Mon, Jan 18
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Tue, Jan 19
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
10:00 amMDW
2h 55m
Nonstop
12:55 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Tue, Jan 19
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Thu, Jan 21
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
11:30 amMDW
4h 55m
STL · 1h 25m
4:25 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Thu, Jan 21
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Fri, Jan 22
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Fri, Jan 22
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Sat, Jan 23
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
9:40 pmMDW
2h 55m
Nonstop
12:35 am+1SAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Sat, Jan 23
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Mon, Jan 25
Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Mon, Jan 11 – Mon, Jan 25
Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT
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 10, 2027 · Return options Jan 12, 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)
2027-01-11 · one way	Southwest Airlines	WN3801 + WN4175	15:20:00→20:00:00 4h 40m 1 stop via STL	Axel-exclusive $155.00	2026-10-29T02:06:15Z
2027-01-11 · one way	Delta Air Lines	DL2497 + DL4688	05:25:00→13:01:00 7h 36m 1 stop via DTW	Axel-exclusive $190.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-12	Southwest Airlines	WN3801 + WN4175 / WN3276	15:20:00→20:00:00 4h 40m 1 stop via STL · 10:00:00→12:55:00 2h 55m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-12	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-13	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:30:00→00:30:00 3h 00m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-13	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-14	Southwest Airlines	WN3801 + WN4175 / WN2737 + WN3075	15:20:00→20:00:00 4h 40m 1 stop via STL · 11:30:00→16:25:00 4h 55m 1 stop via STL	Axel-exclusive $290.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-14	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-15	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:30:00→00:30:00 3h 00m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-15	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-16	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:40:00→00:35:00 2h 55m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-16	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-17	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:30:00→00:30:00 3h 00m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-17	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-18	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:30:00→00:30:00 3h 00m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-18	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-19	Southwest Airlines	WN3801 + WN4175 / WN3276	15:20:00→20:00:00 4h 40m 1 stop via STL · 10:00:00→12:55:00 2h 55m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-19	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-20	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:30:00→00:30:00 3h 00m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-20	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-21	Southwest Airlines	WN3801 + WN4175 / WN2737 + WN3075	15:20:00→20:00:00 4h 40m 1 stop via STL · 11:30:00→16:25:00 4h 55m 1 stop via STL	Axel-exclusive $290.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-21	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-22	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:30:00→00:30:00 3h 00m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-22	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-23	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:40:00→00:35:00 2h 55m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-23	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-24	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:30:00→00:30:00 3h 00m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-24	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-25	Southwest Airlines	WN3801 + WN4175 / WN3024	15:20:00→20:00:00 4h 40m 1 stop via STL · 21:30:00→00:30:00 3h 00m nonstop	Axel-exclusive $300.00	2026-10-29T02:06:15Z
2027-01-11 → 2027-01-25	Delta Air Lines	DL2497 + DL4688 / DL4711 + DL2124	05:25:00→13:01:00 7h 36m 1 stop via DTW · 09:30:00→16:03:00 6h 33m 1 stop via DTW	Axel-exclusive $360.00	2026-10-29T02:06:15Z

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 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $65 total · 4★ Warwick Allerton - Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $254 total
Hotels in Chicago for these nights (Jan 11–13, 2027 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $138 total · 4★ Warwick Allerton - Chicago, $172 total · 5★ Sofitel Chicago Magnificent Mile, $508 total
Hotels in Chicago for these nights (Jan 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $212 total · 4★ Warwick Allerton - Chicago, $260 total · 5★ Sofitel Chicago Magnificent Mile, $762 total
Hotels in Chicago for these nights (Jan 11–15, 2027 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey, $286 total · 4★ Warwick Allerton - Chicago, $349 total · 5★ Sofitel Chicago Magnificent Mile, $976 total
Hotels in Chicago for these nights (Jan 11–16, 2027 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey, $390 total · 4★ Warwick Allerton - Chicago, $440 total · 5★ Sofitel Chicago Magnificent Mile, $1,191 total
Hotels in Chicago for these nights (Jan 11–17, 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, $1,410 total
Hotels in Chicago for these nights (Jan 11–18, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $543 total · 4★ Warwick Allerton - Chicago, $626 total · 5★ Sofitel Chicago Magnificent Mile, $1,633 total
Hotels in Chicago for these nights (Jan 11–19, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $618 total · 4★ Warwick Allerton - Chicago, $718 total · 5★ Sofitel Chicago Magnificent Mile, $1,887 total
Hotels in Chicago for these nights (Jan 11–20, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $693 total · 4★ Warwick Allerton - Chicago, $802 total · 5★ Sofitel Chicago Magnificent Mile, $2,140 total
Hotels in Chicago for these nights (Jan 11–21, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $778 total · 4★ Warwick Allerton - Chicago, $887 total · 5★ Sofitel Chicago Magnificent Mile, $2,350 total
Hotels in Chicago for these nights (Jan 11–22, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $861 total · 4★ Warwick Allerton - Chicago, $976 total · 5★ Sofitel Chicago Magnificent Mile, $2,586 total
Hotels in Chicago for these nights (Jan 11–23, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $936 total · 4★ Warwick Allerton - Chicago, $1,076 total · 5★ Sofitel Chicago Magnificent Mile, $2,796 total
Hotels in Chicago for these nights (Jan 11–24, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,011 total · 4★ Warwick Allerton - Chicago, $1,266 total · 5★ Sofitel Chicago Magnificent Mile, $3,383 total
Hotels in Chicago for these nights (Jan 11–25, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,094 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $1,469 total · 5★ Nobu Hotel Chicago, $5,484 total

All hotels in Chicago

Route overview: San Antonio to Chicago (MDW) flight deals

2027-01-11 · one way · Axel-exclusive $155.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.

2027-01-11 · one way · Axel-exclusive $190.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.

2027-01-11 → 2027-01-12 · Axel-exclusive $300.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN3276: MDW 2027-01-12 10:00:00 → SAT 2027-01-12 12:55:00; nonstop; 175 minutes. Local airport times.

2027-01-11 → 2027-01-12 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-12 09:30:00 → SAT 2027-01-12 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-12 09:30:00 → DTW 2027-01-12 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-12 13:42:00 → SAT 2027-01-12 16:03:00.

2027-01-11 → 2027-01-13 · Axel-exclusive $300.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN3024: MDW 2027-01-13 21:30:00 → SAT 2027-01-14 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-11 → 2027-01-13 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-13 09:30:00 → SAT 2027-01-13 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-13 09:30:00 → DTW 2027-01-13 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-13 13:42:00 → SAT 2027-01-13 16:03:00.

2027-01-11 → 2027-01-14 · Axel-exclusive $290.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN2737 / WN3075: MDW 2027-01-14 11:30:00 → SAT 2027-01-14 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
- WN2737: MDW 2027-01-14 11:30:00 → STL 2027-01-14 12:40:00; layover at STL: 85 minutes.
- WN3075: STL 2027-01-14 14:05:00 → SAT 2027-01-14 16:25:00.

2027-01-11 → 2027-01-14 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-14 09:30:00 → SAT 2027-01-14 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-14 09:30:00 → DTW 2027-01-14 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-14 13:42:00 → SAT 2027-01-14 16:03:00.

2027-01-11 → 2027-01-15 · Axel-exclusive $300.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN3024: MDW 2027-01-15 21:30:00 → SAT 2027-01-16 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-11 → 2027-01-15 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-15 09:30:00 → SAT 2027-01-15 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-15 09:30:00 → DTW 2027-01-15 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-15 13:42:00 → SAT 2027-01-15 16:03:00.

2027-01-11 → 2027-01-17 · Axel-exclusive $300.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN3024: MDW 2027-01-17 21:30:00 → SAT 2027-01-18 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-11 → 2027-01-17 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-17 09:30:00 → SAT 2027-01-17 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-17 09:30:00 → DTW 2027-01-17 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-17 13:42:00 → SAT 2027-01-17 16:03:00.

2027-01-11 → 2027-01-18 · Axel-exclusive $300.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN3024: MDW 2027-01-18 21:30:00 → SAT 2027-01-19 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-11 → 2027-01-18 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-18 09:30:00 → SAT 2027-01-18 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-18 09:30:00 → DTW 2027-01-18 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-18 13:42:00 → SAT 2027-01-18 16:03:00.

2027-01-11 → 2027-01-19 · Axel-exclusive $300.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN3276: MDW 2027-01-19 10:00:00 → SAT 2027-01-19 12:55:00; nonstop; 175 minutes. Local airport times.

2027-01-11 → 2027-01-19 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-19 09:30:00 → SAT 2027-01-19 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-19 09:30:00 → DTW 2027-01-19 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-19 13:42:00 → SAT 2027-01-19 16:03:00.

2027-01-11 → 2027-01-21 · Axel-exclusive $290.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN2737 / WN3075: MDW 2027-01-21 11:30:00 → SAT 2027-01-21 16:25:00; 1 stop(s) via STL; 295 minutes. Local airport times.
- WN2737: MDW 2027-01-21 11:30:00 → STL 2027-01-21 12:40:00; layover at STL: 85 minutes.
- WN3075: STL 2027-01-21 14:05:00 → SAT 2027-01-21 16:25:00.

2027-01-11 → 2027-01-21 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-21 09:30:00 → SAT 2027-01-21 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-21 09:30:00 → DTW 2027-01-21 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-21 13:42:00 → SAT 2027-01-21 16:03:00.

2027-01-11 → 2027-01-22 · Axel-exclusive $300.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN3024: MDW 2027-01-22 21:30:00 → SAT 2027-01-23 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-11 → 2027-01-22 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-22 09:30:00 → SAT 2027-01-22 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-22 09:30:00 → DTW 2027-01-22 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-22 13:42:00 → SAT 2027-01-22 16:03:00.

2027-01-11 → 2027-01-23 · Axel-exclusive $300.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN3024: MDW 2027-01-23 21:40:00 → SAT 2027-01-24 00:35:00; nonstop; 175 minutes. Local airport times.

2027-01-11 → 2027-01-23 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-23 09:30:00 → SAT 2027-01-23 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-23 09:30:00 → DTW 2027-01-23 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-23 13:42:00 → SAT 2027-01-23 16:03:00.

2027-01-11 → 2027-01-25 · Axel-exclusive $300.00

Southwest Airlines WN3801 / WN4175: SAT 2027-01-11 15:20:00 → MDW 2027-01-11 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
- WN3801: SAT 2027-01-11 15:20:00 → STL 2027-01-11 17:20:00; layover at STL: 95 minutes.
- WN4175: STL 2027-01-11 18:55:00 → MDW 2027-01-11 20:00:00.
Southwest Airlines WN3024: MDW 2027-01-25 21:30:00 → SAT 2027-01-26 00:30:00; nonstop; 180 minutes. Local airport times.

2027-01-11 → 2027-01-25 · Axel-exclusive $360.00

Delta Air Lines DL2497 / DL4688: SAT 2027-01-11 05:25:00 → MDW 2027-01-11 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
- DL2497: SAT 2027-01-11 05:25:00 → DTW 2027-01-11 09:28:00; layover at DTW: 196 minutes.
- DL4688: DTW 2027-01-11 12:44:00 → MDW 2027-01-11 13:01:00.
Delta Air Lines DL4711 / DL2124: MDW 2027-01-25 09:30:00 → SAT 2027-01-25 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
- DL4711: MDW 2027-01-25 09:30:00 → DTW 2027-01-25 11:45:00; layover at DTW: 117 minutes.
- DL2124: DTW 2027-01-25 13:42:00 → SAT 2027-01-25 16:03:00.

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This page: San Antonio (SAT) to Chicago (MDW) · Jan 11, 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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