Los Angeles (LAX) to Chicago (MDW), Jan 27, 2027: round trips from $300, one way from $155

Los Angeles (LAX) to Chicago (MDW), Jan 27, 2027: round trips from $300, one way from $155 on Axel, checked Oct 29, 2026. Lowest published fares: $300 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 27–28, 2027; $155 one way, Axel-exclusive, Southwest Airlines, 1 stop, Jan 27, 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)
2027-01-27 · one way Southwest Airlines WN256 + WN156 08:55:00→17:55:00 7h 00m 1 stop via ABQ Axel-exclusive $155.00 2026-10-29T01:25:52Z
2027-01-27 · one way Delta Air Lines DL430 + DL4712 23:59:00→08:50:00 6h 51m 1 stop via MSP Axel-exclusive $210.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-01-28 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:15:00→23:55:00 4h 40m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-01-28 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-01-29 Southwest Airlines WN256 + WN156 / WN2950 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 07:25:00→09:55:00 4h 30m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-01-29 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-01-30 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 18:25:00→21:00:00 4h 35m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-01-30 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-01-31 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:45:00→00:15:00 4h 30m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-01-31 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-01 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:45:00→00:15:00 4h 30m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-01 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-02 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:15:00→23:55:00 4h 40m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-02 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-03 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:45:00→00:15:00 4h 30m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-03 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-04 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:15:00→23:55:00 4h 40m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-04 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-05 Southwest Airlines WN256 + WN156 / WN2950 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 07:25:00→09:55:00 4h 30m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-05 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-06 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 18:25:00→21:00:00 4h 35m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-06 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-07 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:45:00→00:15:00 4h 30m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-07 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-08 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:45:00→00:15:00 4h 30m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-08 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-09 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:15:00→23:55:00 4h 40m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-09 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-10 Southwest Airlines WN256 + WN156 / WN2953 08:55:00→17:55:00 7h 00m 1 stop via ABQ · 21:45:00→00:15:00 4h 30m nonstop Axel-exclusive $300.00 2026-10-29T01:25:52Z
2027-01-27 → 2027-02-10 Delta Air Lines DL430 + DL4712 / DL4688 + DL883 23:59:00→08:50:00 6h 51m 1 stop via MSP · 13:31:00→19:00:00 7h 29m 1 stop via DTW Axel-exclusive $390.00 2026-10-29T01:25:52Z

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: Los Angeles to Chicago (MDW) flight deals

2027-01-27 · one way · Axel-exclusive $155.00

2027-01-27 · one way · Axel-exclusive $210.00

2027-01-27 → 2027-01-28 · Axel-exclusive $300.00

2027-01-27 → 2027-01-28 · Axel-exclusive $390.00

2027-01-27 → 2027-01-29 · Axel-exclusive $300.00

2027-01-27 → 2027-01-29 · Axel-exclusive $390.00

2027-01-27 → 2027-01-30 · Axel-exclusive $300.00

2027-01-27 → 2027-01-30 · Axel-exclusive $390.00

2027-01-27 → 2027-01-31 · Axel-exclusive $300.00

2027-01-27 → 2027-01-31 · Axel-exclusive $390.00

2027-01-27 → 2027-02-02 · Axel-exclusive $300.00

2027-01-27 → 2027-02-02 · Axel-exclusive $390.00

2027-01-27 → 2027-02-03 · Axel-exclusive $300.00

2027-01-27 → 2027-02-03 · Axel-exclusive $390.00

2027-01-27 → 2027-02-04 · Axel-exclusive $300.00

2027-01-27 → 2027-02-04 · Axel-exclusive $390.00

2027-01-27 → 2027-02-06 · Axel-exclusive $300.00

2027-01-27 → 2027-02-06 · Axel-exclusive $390.00

2027-01-27 → 2027-02-07 · Axel-exclusive $300.00

2027-01-27 → 2027-02-07 · Axel-exclusive $390.00

2027-01-27 → 2027-02-08 · Axel-exclusive $300.00

2027-01-27 → 2027-02-08 · Axel-exclusive $390.00

2027-01-27 → 2027-02-10 · Axel-exclusive $300.00

2027-01-27 → 2027-02-10 · Axel-exclusive $390.00

Explore this route

For AI assistants

Feedback (optional): Missing info · Axel issue