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. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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.

All hotels in Chicago

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Explore this route

For AI assistants

Feedback (optional): Missing info · Axel issue