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Chicago → San Francisco

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MDW → SFO1 adulteconomy

22 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
9:05 pmMDW
4h 50m
Nonstop
11:55 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

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

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
9:55 amMDW
4h 50m
Nonstop
12:45 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:35 pmMDW
6h 45m
DEN · 1h 20m
7:20 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:05 pmMDW
7h 50m
PHX · 1h 45m
11:55 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
10:00 amMDW
7h 45m
LAS · 2h 5m
3:45 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
9:55 amMDW
7h 55m
BNA · 1h 20m
3:50 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
2:35 pmMDW
6h 45m
DEN · 1h 20m
7:20 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Show 6 more flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
1:55 pmMDW
8h 5m
AUS · 1h 25m
8:00 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
9:55 amMDW
4h 50m
Nonstop
12:45 pmSFO
Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
10:00 amMDW
7h 45m
LAS · 2h 5m
3:45 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
9:55 amMDW
7h 55m
BNA · 1h 20m
3:50 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
6:05 pmMDW
7h 50m
PHX · 1h 45m
11:55 pmSFO
Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
9:55 amMDW
4h 50m
Nonstop
12:45 pmSFO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
1:31 pmMDW
7h 45m
DTW · 1h 15m
7:16 pmSFO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
9:05 pmMDW
4h 50m
Nonstop
11:55 pmSFO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
9:55 amMDW
7h 55m
BNA · 1h 20m
3:50 pmSFO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:35 pmMDW
6h 45m
DEN · 1h 20m
7:20 pmSFO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
6:05 pmMDW
7h 50m
PHX · 1h 45m
11:55 pmSFO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
10:00 amMDW
7h 45m
LAS · 2h 5m
3:45 pmSFO

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
1:55 pmMDW
8h 5m
AUS · 1h 25m
8:00 pmSFO

One-way total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ SFO

Economy

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

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Why book with Axel
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  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
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Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 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)
2026-11-20 · one waySouthwest AirlinesWN786$170.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1536 / WN2331$379.502026-10-29T01:29:13Z
2026-11-20 · one wayDelta Air LinesDL4688 + DL442$185.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Delta Air LinesDL4688 + DL442 / DL570 + DL1728$402.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN1536$170.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN786 / WN2331$379.502026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN725 + WN4254$155.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN4606 + WN1817$155.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2998 + WN1448$155.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN142 + WN2440$155.002026-10-29T01:29:13Z
2026-11-20 · one waySouthwest AirlinesWN2891 + WN4893$155.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4606 + WN1817 / WN3847 + WN2515$345.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2998 + WN1448 / WN3847 + WN2515$345.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN142 + WN2440 / WN3847 + WN2515$345.002026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN725 + WN4254 / WN3847 + WN2515$345.002026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4606 + WN1817 / WN2331$364.502026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2891 + WN4893 / WN2331$364.502026-10-29T01:29:13Z
2026-11-27 → 2026-12-04Southwest AirlinesWN786 / WN3847 + WN2515$364.502026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN142 + WN2440 / WN2331$364.502026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN725 + WN4254 / WN2331$364.502026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2998 + WN1448 / WN2331$364.502026-10-29T01:29:13Z
2026-11-20 → 2026-11-23Delta Air LinesDL4688 + DL442 / DL570 + DL1728$402.502026-10-29T01:29:13Z

2026-11-20 · one way · $170.00

  • Southwest Airlines WN786: MDW 2026-11-20 09:55:00 → SFO 2026-11-20 12:45:00; nonstop; 290 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $379.50

  • Southwest Airlines WN1536: MDW 2026-11-20 21:05:00 → SFO 2026-11-20 23:55:00; nonstop; 290 minutes. Local airport times.
  • Southwest Airlines WN2331: SFO 2026-11-23 06:00:00 → MDW 2026-11-23 12:15:00; nonstop; 255 minutes. Local airport times.

2026-11-20 · one way · $185.00

  • Delta Air Lines DL4688 / DL442: MDW 2026-11-20 13:31:00 → SFO 2026-11-20 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-11-20 13:31:00 → DTW 2026-11-20 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-11-20 16:59:00 → SFO 2026-11-20 19:16:00.

2026-11-27 → 2026-12-04 · $402.50

  • Delta Air Lines DL4688 / DL442: MDW 2026-11-27 13:31:00 → SFO 2026-11-27 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-11-27 13:31:00 → DTW 2026-11-27 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-11-27 16:59:00 → SFO 2026-11-27 19:16:00.
  • Delta Air Lines DL570 / DL1728: SFO 2026-12-04 06:00:00 → MDW 2026-12-04 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-04 06:00:00 → ATL 2026-12-04 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-04 15:25:00 → MDW 2026-12-04 16:18:00.

2026-11-20 · one way · $170.00

  • Southwest Airlines WN1536: MDW 2026-11-20 21:05:00 → SFO 2026-11-20 23:55:00; nonstop; 290 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $379.50

  • Southwest Airlines WN786: MDW 2026-11-20 09:55:00 → SFO 2026-11-20 12:45:00; nonstop; 290 minutes. Local airport times.
  • Southwest Airlines WN2331: SFO 2026-11-23 06:00:00 → MDW 2026-11-23 12:15:00; nonstop; 255 minutes. Local airport times.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN725 / WN4254: MDW 2026-11-20 09:55:00 → SFO 2026-11-20 15:50:00; 1 stop(s) via BNA; 475 minutes. Local airport times.
    • WN725: MDW 2026-11-20 09:55:00 → BNA 2026-11-20 11:30:00; layover at BNA: 80 minutes.
    • WN4254: BNA 2026-11-20 12:50:00 → SFO 2026-11-20 15:50:00.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN4606 / WN1817: MDW 2026-11-20 14:35:00 → SFO 2026-11-20 19:20:00; 1 stop(s) via DEN; 405 minutes. Local airport times.
    • WN4606: MDW 2026-11-20 14:35:00 → DEN 2026-11-20 16:15:00; layover at DEN: 80 minutes.
    • WN1817: DEN 2026-11-20 17:35:00 → SFO 2026-11-20 19:20:00.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN2998 / WN1448: MDW 2026-11-20 18:05:00 → SFO 2026-11-20 23:55:00; 1 stop(s) via PHX; 470 minutes. Local airport times.
    • WN2998: MDW 2026-11-20 18:05:00 → PHX 2026-11-20 21:00:00; layover at PHX: 105 minutes.
    • WN1448: PHX 2026-11-20 22:45:00 → SFO 2026-11-20 23:55:00.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN142 / WN2440: MDW 2026-11-20 10:00:00 → SFO 2026-11-20 15:45:00; 1 stop(s) via LAS; 465 minutes. Local airport times.
    • WN142: MDW 2026-11-20 10:00:00 → LAS 2026-11-20 11:55:00; layover at LAS: 125 minutes.
    • WN2440: LAS 2026-11-20 14:00:00 → SFO 2026-11-20 15:45:00.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN2891 / WN4893: MDW 2026-11-20 13:55:00 → SFO 2026-11-20 20:00:00; 1 stop(s) via AUS; 485 minutes. Local airport times.
    • WN2891: MDW 2026-11-20 13:55:00 → AUS 2026-11-20 16:35:00; layover at AUS: 85 minutes.
    • WN4893: AUS 2026-11-20 18:00:00 → SFO 2026-11-20 20:00:00.

2026-11-27 → 2026-12-04 · $345.00

  • Southwest Airlines WN4606 / WN1817: MDW 2026-11-27 14:35:00 → SFO 2026-11-27 19:20:00; 1 stop(s) via DEN; 405 minutes. Local airport times.
    • WN4606: MDW 2026-11-27 14:35:00 → DEN 2026-11-27 16:15:00; layover at DEN: 80 minutes.
    • WN1817: DEN 2026-11-27 17:35:00 → SFO 2026-11-27 19:20:00.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-04 08:20:00 → MDW 2026-12-04 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-04 08:20:00 → LAX 2026-12-04 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-04 11:15:00 → MDW 2026-12-04 17:15:00.

2026-11-27 → 2026-12-04 · $345.00

  • Southwest Airlines WN2998 / WN1448: MDW 2026-11-27 18:05:00 → SFO 2026-11-27 23:55:00; 1 stop(s) via PHX; 470 minutes. Local airport times.
    • WN2998: MDW 2026-11-27 18:05:00 → PHX 2026-11-27 21:00:00; layover at PHX: 105 minutes.
    • WN1448: PHX 2026-11-27 22:45:00 → SFO 2026-11-27 23:55:00.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-04 08:20:00 → MDW 2026-12-04 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-04 08:20:00 → LAX 2026-12-04 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-04 11:15:00 → MDW 2026-12-04 17:15:00.

2026-11-27 → 2026-12-04 · $345.00

  • Southwest Airlines WN142 / WN2440: MDW 2026-11-27 10:00:00 → SFO 2026-11-27 15:45:00; 1 stop(s) via LAS; 465 minutes. Local airport times.
    • WN142: MDW 2026-11-27 10:00:00 → LAS 2026-11-27 11:55:00; layover at LAS: 125 minutes.
    • WN2440: LAS 2026-11-27 14:00:00 → SFO 2026-11-27 15:45:00.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-04 08:20:00 → MDW 2026-12-04 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-04 08:20:00 → LAX 2026-12-04 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-04 11:15:00 → MDW 2026-12-04 17:15:00.

2026-11-27 → 2026-12-04 · $345.00

  • Southwest Airlines WN725 / WN4254: MDW 2026-11-27 09:55:00 → SFO 2026-11-27 15:50:00; 1 stop(s) via BNA; 475 minutes. Local airport times.
    • WN725: MDW 2026-11-27 09:55:00 → BNA 2026-11-27 11:30:00; layover at BNA: 80 minutes.
    • WN4254: BNA 2026-11-27 12:50:00 → SFO 2026-11-27 15:50:00.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-04 08:20:00 → MDW 2026-12-04 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-04 08:20:00 → LAX 2026-12-04 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-04 11:15:00 → MDW 2026-12-04 17:15:00.

2026-11-20 → 2026-11-23 · $364.50

  • Southwest Airlines WN4606 / WN1817: MDW 2026-11-20 14:35:00 → SFO 2026-11-20 19:20:00; 1 stop(s) via DEN; 405 minutes. Local airport times.
    • WN4606: MDW 2026-11-20 14:35:00 → DEN 2026-11-20 16:15:00; layover at DEN: 80 minutes.
    • WN1817: DEN 2026-11-20 17:35:00 → SFO 2026-11-20 19:20:00.
  • Southwest Airlines WN2331: SFO 2026-11-23 06:00:00 → MDW 2026-11-23 12:15:00; nonstop; 255 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $364.50

  • Southwest Airlines WN2891 / WN4893: MDW 2026-11-20 13:55:00 → SFO 2026-11-20 20:00:00; 1 stop(s) via AUS; 485 minutes. Local airport times.
    • WN2891: MDW 2026-11-20 13:55:00 → AUS 2026-11-20 16:35:00; layover at AUS: 85 minutes.
    • WN4893: AUS 2026-11-20 18:00:00 → SFO 2026-11-20 20:00:00.
  • Southwest Airlines WN2331: SFO 2026-11-23 06:00:00 → MDW 2026-11-23 12:15:00; nonstop; 255 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $364.50

  • Southwest Airlines WN786: MDW 2026-11-27 09:55:00 → SFO 2026-11-27 12:45:00; nonstop; 290 minutes. Local airport times.
  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-04 08:20:00 → MDW 2026-12-04 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-04 08:20:00 → LAX 2026-12-04 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-04 11:15:00 → MDW 2026-12-04 17:15:00.

2026-11-20 → 2026-11-23 · $364.50

  • Southwest Airlines WN142 / WN2440: MDW 2026-11-20 10:00:00 → SFO 2026-11-20 15:45:00; 1 stop(s) via LAS; 465 minutes. Local airport times.
    • WN142: MDW 2026-11-20 10:00:00 → LAS 2026-11-20 11:55:00; layover at LAS: 125 minutes.
    • WN2440: LAS 2026-11-20 14:00:00 → SFO 2026-11-20 15:45:00.
  • Southwest Airlines WN2331: SFO 2026-11-23 06:00:00 → MDW 2026-11-23 12:15:00; nonstop; 255 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $364.50

  • Southwest Airlines WN725 / WN4254: MDW 2026-11-20 09:55:00 → SFO 2026-11-20 15:50:00; 1 stop(s) via BNA; 475 minutes. Local airport times.
    • WN725: MDW 2026-11-20 09:55:00 → BNA 2026-11-20 11:30:00; layover at BNA: 80 minutes.
    • WN4254: BNA 2026-11-20 12:50:00 → SFO 2026-11-20 15:50:00.
  • Southwest Airlines WN2331: SFO 2026-11-23 06:00:00 → MDW 2026-11-23 12:15:00; nonstop; 255 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $364.50

  • Southwest Airlines WN2998 / WN1448: MDW 2026-11-20 18:05:00 → SFO 2026-11-20 23:55:00; 1 stop(s) via PHX; 470 minutes. Local airport times.
    • WN2998: MDW 2026-11-20 18:05:00 → PHX 2026-11-20 21:00:00; layover at PHX: 105 minutes.
    • WN1448: PHX 2026-11-20 22:45:00 → SFO 2026-11-20 23:55:00.
  • Southwest Airlines WN2331: SFO 2026-11-23 06:00:00 → MDW 2026-11-23 12:15:00; nonstop; 255 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $402.50

  • Delta Air Lines DL4688 / DL442: MDW 2026-11-20 13:31:00 → SFO 2026-11-20 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-11-20 13:31:00 → DTW 2026-11-20 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-11-20 16:59:00 → SFO 2026-11-20 19:16:00.
  • Delta Air Lines DL570 / DL1728: SFO 2026-11-23 06:00:00 → MDW 2026-11-23 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-11-23 06:00:00 → ATL 2026-11-23 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-11-23 15:25:00 → MDW 2026-11-23 16:18:00.

More dates for this route