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San Francisco → Chicago

Jan 21, 2027 · return Jan 24, 2027

SFO → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW
Southwest Airlines
9:30 pmMDW
4h 55m
Nonstop
12:25 am+1SFO

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
11:35 pmSFO
4h 25m
Nonstop
6:00 am+1MDW
Southwest Airlines
9:30 pmMDW
4h 55m
Nonstop
12:25 am+1SFO

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 – Sun, Jan 24

Delta Air Lines
6:00 amSFO
8h 18m
ATL · 1h 56m
4:18 pmMDW
Delta Air Lines
1:31 pmMDW
7h 45m
DTW · 1h 15m
7:16 pmSFO

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
8:00 amSFO
7h 55m
DEN · 3h 10m
5:55 pmMDW
Southwest Airlines
9:30 pmMDW
4h 55m
Nonstop
12:25 am+1SFO

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
8:20 pmSFO
7h 25m
PHX · 2h
5:45 am+1MDW
Southwest Airlines
9:30 pmMDW
4h 55m
Nonstop
12:25 am+1SFO

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW
Southwest Airlines
9:30 pmMDW
4h 55m
Nonstop
12:25 am+1SFO

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Southwest Airlines
1:05 pmSFO
7h 55m
STL · 2h 55m
11:00 pmMDW
Southwest Airlines
9:30 pmMDW
4h 55m
Nonstop
12:25 am+1SFO

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Sun, Jan 24

Delta Air Lines
6:00 amSFO
8h 39m
MSP · 3h 20m
4:39 pmMDW
Delta Air Lines
1:31 pmMDW
7h 45m
DTW · 1h 15m
7:16 pmSFO

Round-trip total · 1 adult · Taxes included

Make this trip yours

SFO ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
For AI assistants: every fare, every link, instructions

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

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-21 → 2027-01-24Southwest AirlinesWN2331 / WN4836$332.502026-10-29T01:18:59Z
2027-01-21 → 2027-01-24Delta Air LinesDL570 + DL1728 / DL4688 + DL442$370.502026-10-29T01:18:59Z
2027-01-21 → 2027-01-24Southwest AirlinesWN3849 / WN4836$332.502026-10-29T01:18:59Z
2027-01-21 → 2027-01-24Southwest AirlinesWN3428 + WN1699 / WN4836$313.502026-10-29T01:18:59Z
2027-01-21 → 2027-01-24Southwest AirlinesWN2749 + WN4963 / WN4836$313.502026-10-29T01:18:59Z
2027-01-21 → 2027-01-24Southwest AirlinesWN3847 + WN2515 / WN4836$313.502026-10-29T01:18:59Z
2027-01-21 → 2027-01-24Southwest AirlinesWN2989 + WN4770 / WN4836$313.502026-10-29T01:18:59Z
2027-01-21 → 2027-01-24Delta Air LinesDL2178 + DL4714 / DL4688 + DL442$370.502026-10-29T01:18:59Z

2027-01-21 → 2027-01-24 · $332.50

  • Southwest Airlines WN2331: SFO 2027-01-21 06:00:00 → MDW 2027-01-21 12:15:00; nonstop; 255 minutes. Local airport times.
  • Southwest Airlines WN4836: MDW 2027-01-24 21:30:00 → SFO 2027-01-25 00:25:00; nonstop; 295 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $370.50

  • Delta Air Lines DL570 / DL1728: SFO 2027-01-21 06:00:00 → MDW 2027-01-21 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2027-01-21 06:00:00 → ATL 2027-01-21 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2027-01-21 15:25:00 → MDW 2027-01-21 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2027-01-24 13:31:00 → SFO 2027-01-24 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2027-01-24 13:31:00 → DTW 2027-01-24 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2027-01-24 16:59:00 → SFO 2027-01-24 19:16:00.

2027-01-21 → 2027-01-24 · $332.50

  • Southwest Airlines WN3849: SFO 2027-01-21 23:35:00 → MDW 2027-01-22 06:00:00; nonstop; 265 minutes. Local airport times.
  • Southwest Airlines WN4836: MDW 2027-01-24 21:30:00 → SFO 2027-01-25 00:25:00; nonstop; 295 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $313.50

  • Southwest Airlines WN3428 / WN1699: SFO 2027-01-21 08:00:00 → MDW 2027-01-21 17:55:00; 1 stop(s) via DEN; 475 minutes. Local airport times.
    • WN3428: SFO 2027-01-21 08:00:00 → DEN 2027-01-21 11:30:00; layover at DEN: 190 minutes.
    • WN1699: DEN 2027-01-21 14:40:00 → MDW 2027-01-21 17:55:00.
  • Southwest Airlines WN4836: MDW 2027-01-24 21:30:00 → SFO 2027-01-25 00:25:00; nonstop; 295 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $313.50

  • Southwest Airlines WN2749 / WN4963: SFO 2027-01-21 20:20:00 → MDW 2027-01-22 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2027-01-21 20:20:00 → PHX 2027-01-21 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2027-01-22 01:35:00 → MDW 2027-01-22 05:45:00.
  • Southwest Airlines WN4836: MDW 2027-01-24 21:30:00 → SFO 2027-01-25 00:25:00; nonstop; 295 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $313.50

  • Southwest Airlines WN3847 / WN2515: SFO 2027-01-21 08:20:00 → MDW 2027-01-21 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2027-01-21 08:20:00 → LAX 2027-01-21 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2027-01-21 11:15:00 → MDW 2027-01-21 17:15:00.
  • Southwest Airlines WN4836: MDW 2027-01-24 21:30:00 → SFO 2027-01-25 00:25:00; nonstop; 295 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $313.50

  • Southwest Airlines WN2989 / WN4770: SFO 2027-01-21 13:05:00 → MDW 2027-01-21 23:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
    • WN2989: SFO 2027-01-21 13:05:00 → STL 2027-01-21 18:55:00; layover at STL: 175 minutes.
    • WN4770: STL 2027-01-21 21:50:00 → MDW 2027-01-21 23:00:00.
  • Southwest Airlines WN4836: MDW 2027-01-24 21:30:00 → SFO 2027-01-25 00:25:00; nonstop; 295 minutes. Local airport times.

2027-01-21 → 2027-01-24 · $370.50

  • Delta Air Lines DL2178 / DL4714: SFO 2027-01-21 06:00:00 → MDW 2027-01-21 16:39:00; 1 stop(s) via MSP; 519 minutes. Local airport times.
    • DL2178: SFO 2027-01-21 06:00:00 → MSP 2027-01-21 11:40:00; layover at MSP: 200 minutes.
    • DL4714: MSP 2027-01-21 15:00:00 → MDW 2027-01-21 16:39:00.
  • Delta Air Lines DL4688 / DL442: MDW 2027-01-24 13:31:00 → SFO 2027-01-24 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2027-01-24 13:31:00 → DTW 2027-01-24 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2027-01-24 16:59:00 → SFO 2027-01-24 19:16:00.

More dates for this route