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

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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.

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 $81 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $54 · 5★ Sofitel Chicago Magnificent Mile $206

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★ The Chicago Hotel Collection River North $158 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $125 · 5★ Sofitel Chicago Magnificent Mile $416

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★ The Chicago Hotel Collection River North $231 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $144 · 5★ Sofitel Chicago Magnificent Mile $615

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★ The Chicago Hotel Collection River North $304 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $163 · 5★ Sofitel Chicago Magnificent Mile $825

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★ The Chicago Hotel Collection River North $374 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $189 · 5★ Sofitel Chicago Magnificent Mile $1,083

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 $447 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $215 · 5★ Sofitel Chicago Magnificent Mile $1,341

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 $528 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $234 · 5★ Sofitel Chicago Magnificent Mile $1,547

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 $601 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $305 · 5★ Sofitel Chicago Magnificent Mile $1,774

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 $685 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $376 · 5★ Sofitel Chicago Magnificent Mile $1,980

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 $770 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $447 · 5★ Sofitel Chicago Magnificent Mile $2,238

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 $843 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $466 · 5★ Sofitel Chicago Magnificent Mile $2,447

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 $916 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $563 · 5★ Sofitel Chicago Magnificent Mile $2,696

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 $989 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $660 · 5★ Sofitel Chicago Magnificent Mile $3,283

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 $1,059 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $740 · 5★ Nobu Hotel Chicago $5,011

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, $81 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $54 total · 5★ Sofitel Chicago Magnificent Mile, $206 total
Hotels in Chicago for these nights (Jan 11–13, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $158 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $125 total · 5★ Sofitel Chicago Magnificent Mile, $416 total
Hotels in Chicago for these nights (Jan 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $144 total · 5★ Sofitel Chicago Magnificent Mile, $615 total
Hotels in Chicago for these nights (Jan 11–15, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $304 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $163 total · 5★ Sofitel Chicago Magnificent Mile, $825 total
Hotels in Chicago for these nights (Jan 11–16, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $374 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $189 total · 5★ Sofitel Chicago Magnificent Mile, $1,083 total
Hotels in Chicago for these nights (Jan 11–17, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $447 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $215 total · 5★ Sofitel Chicago Magnificent Mile, $1,341 total
Hotels in Chicago for these nights (Jan 11–18, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $528 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $234 total · 5★ Sofitel Chicago Magnificent Mile, $1,547 total
Hotels in Chicago for these nights (Jan 11–19, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $601 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $305 total · 5★ Sofitel Chicago Magnificent Mile, $1,774 total
Hotels in Chicago for these nights (Jan 11–20, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $685 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $376 total · 5★ Sofitel Chicago Magnificent Mile, $1,980 total
Hotels in Chicago for these nights (Jan 11–21, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $770 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $447 total · 5★ Sofitel Chicago Magnificent Mile, $2,238 total
Hotels in Chicago for these nights (Jan 11–22, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $843 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $466 total · 5★ Sofitel Chicago Magnificent Mile, $2,447 total
Hotels in Chicago for these nights (Jan 11–23, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $916 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $563 total · 5★ Sofitel Chicago Magnificent Mile, $2,696 total
Hotels in Chicago for these nights (Jan 11–24, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $989 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $660 total · 5★ Sofitel Chicago Magnificent Mile, $3,283 total
Hotels in Chicago for these nights (Jan 11–25, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,059 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $740 total · 5★ Nobu Hotel Chicago, $5,011 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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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 San Antonio to Chicago (MDW) 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.