Travel with Axel,
get the best price.

San Francisco → Chicago

Dec 9, 2026 · return Dec 15, 2026

SFO → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Wed, Dec 9 – Tue, Dec 15

Southwest Airlines
11:35 pmSFO
4h 25m
Nonstop
6:00 am+1MDW
Southwest Airlines
9:05 pmMDW
4h 50m
Nonstop
11:55 pmSFO

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Tue, Dec 15

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

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Dec 9 – Tue, Dec 15

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

Wed, Dec 9 – Tue, Dec 15

Southwest Airlines
8:00 amSFO
7h 55m
DEN · 3h 10m
5:55 pmMDW
Southwest Airlines
9:05 pmMDW
4h 50m
Nonstop
11:55 pmSFO

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Tue, Dec 15

Southwest Airlines
8:20 pmSFO
7h 25m
PHX · 2h
5:45 am+1MDW
Southwest Airlines
9:05 pmMDW
4h 50m
Nonstop
11:55 pmSFO

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Tue, Dec 15

Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW
Southwest Airlines
9:05 pmMDW
4h 50m
Nonstop
11:55 pmSFO

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Tue, Dec 15

Southwest Airlines
1:05 pmSFO
7h 55m
STL · 2h 55m
11:00 pmMDW
Southwest Airlines
9:05 pmMDW
4h 50m
Nonstop
11:55 pmSFO

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Tue, Dec 15

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.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

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

All dates for this routeNov 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 2027Oct 30, 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)
2026-12-09 → 2026-12-15Southwest AirlinesWN3849 / WN1536$350.002026-10-29T01:18:59Z
2026-12-09 → 2026-12-15Delta Air LinesDL570 + DL1728 / DL4688 + DL442$390.002026-10-29T01:18:59Z
2026-12-09 → 2026-12-15Southwest AirlinesWN2331 / WN1536$350.002026-10-29T01:18:59Z
2026-12-09 → 2026-12-15Southwest AirlinesWN3428 + WN1699 / WN1536$330.002026-10-29T01:18:59Z
2026-12-09 → 2026-12-15Southwest AirlinesWN2749 + WN4963 / WN1536$330.002026-10-29T01:18:59Z
2026-12-09 → 2026-12-15Southwest AirlinesWN3847 + WN2515 / WN1536$330.002026-10-29T01:18:59Z
2026-12-09 → 2026-12-15Southwest AirlinesWN2989 + WN4770 / WN1536$330.002026-10-29T01:18:59Z
2026-12-09 → 2026-12-15Delta Air LinesDL2178 + DL4714 / DL4688 + DL442$390.002026-10-29T01:18:59Z

2026-12-09 → 2026-12-15 · $350.00

  • Southwest Airlines WN3849: SFO 2026-12-09 23:35:00 → MDW 2026-12-10 06:00:00; nonstop; 265 minutes. Local airport times.
  • Southwest Airlines WN1536: MDW 2026-12-15 21:05:00 → SFO 2026-12-15 23:55:00; nonstop; 290 minutes. Local airport times.

2026-12-09 → 2026-12-15 · $390.00

  • Delta Air Lines DL570 / DL1728: SFO 2026-12-09 06:00:00 → MDW 2026-12-09 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2026-12-09 06:00:00 → ATL 2026-12-09 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2026-12-09 15:25:00 → MDW 2026-12-09 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-15 13:31:00 → SFO 2026-12-15 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-15 13:31:00 → DTW 2026-12-15 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-15 16:59:00 → SFO 2026-12-15 19:16:00.

2026-12-09 → 2026-12-15 · $350.00

  • Southwest Airlines WN2331: SFO 2026-12-09 06:00:00 → MDW 2026-12-09 12:15:00; nonstop; 255 minutes. Local airport times.
  • Southwest Airlines WN1536: MDW 2026-12-15 21:05:00 → SFO 2026-12-15 23:55:00; nonstop; 290 minutes. Local airport times.

2026-12-09 → 2026-12-15 · $330.00

  • Southwest Airlines WN3428 / WN1699: SFO 2026-12-09 08:00:00 → MDW 2026-12-09 17:55:00; 1 stop(s) via DEN; 475 minutes. Local airport times.
    • WN3428: SFO 2026-12-09 08:00:00 → DEN 2026-12-09 11:30:00; layover at DEN: 190 minutes.
    • WN1699: DEN 2026-12-09 14:40:00 → MDW 2026-12-09 17:55:00.
  • Southwest Airlines WN1536: MDW 2026-12-15 21:05:00 → SFO 2026-12-15 23:55:00; nonstop; 290 minutes. Local airport times.

2026-12-09 → 2026-12-15 · $330.00

  • Southwest Airlines WN2749 / WN4963: SFO 2026-12-09 20:20:00 → MDW 2026-12-10 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2026-12-09 20:20:00 → PHX 2026-12-09 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2026-12-10 01:35:00 → MDW 2026-12-10 05:45:00.
  • Southwest Airlines WN1536: MDW 2026-12-15 21:05:00 → SFO 2026-12-15 23:55:00; nonstop; 290 minutes. Local airport times.

2026-12-09 → 2026-12-15 · $330.00

  • Southwest Airlines WN3847 / WN2515: SFO 2026-12-09 08:20:00 → MDW 2026-12-09 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2026-12-09 08:20:00 → LAX 2026-12-09 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2026-12-09 11:15:00 → MDW 2026-12-09 17:15:00.
  • Southwest Airlines WN1536: MDW 2026-12-15 21:05:00 → SFO 2026-12-15 23:55:00; nonstop; 290 minutes. Local airport times.

2026-12-09 → 2026-12-15 · $330.00

  • Southwest Airlines WN2989 / WN4770: SFO 2026-12-09 13:05:00 → MDW 2026-12-09 23:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
    • WN2989: SFO 2026-12-09 13:05:00 → STL 2026-12-09 18:55:00; layover at STL: 175 minutes.
    • WN4770: STL 2026-12-09 21:50:00 → MDW 2026-12-09 23:00:00.
  • Southwest Airlines WN1536: MDW 2026-12-15 21:05:00 → SFO 2026-12-15 23:55:00; nonstop; 290 minutes. Local airport times.

2026-12-09 → 2026-12-15 · $390.00

  • Delta Air Lines DL2178 / DL4714: SFO 2026-12-09 06:00:00 → MDW 2026-12-09 16:39:00; 1 stop(s) via MSP; 519 minutes. Local airport times.
    • DL2178: SFO 2026-12-09 06:00:00 → MSP 2026-12-09 11:40:00; layover at MSP: 200 minutes.
    • DL4714: MSP 2026-12-09 15:00:00 → MDW 2026-12-09 16:39:00.
  • Delta Air Lines DL4688 / DL442: MDW 2026-12-15 13:31:00 → SFO 2026-12-15 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2026-12-15 13:31:00 → DTW 2026-12-15 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2026-12-15 16:59:00 → SFO 2026-12-15 19:16:00.

More dates for this route