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Route overview: San Francisco Bay Area to Chicago (MDW) flight deals

San Francisco → Chicago

Feb 6, 2027 · return Feb 13, 2027

SFO → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Sat, Feb 6 – Sat, Feb 13

Southwest Airlines
11:35 pmSFO
4h 25m
Nonstop
6:00 am+1MDW
Southwest Airlines
10:00 amMDW
4h 50m
Nonstop
12:50 pmSFO

Round-trip total · 1 adult · Taxes included

Sat, Feb 6 – Sat, Feb 13

Southwest Airlines
6:00 amSFO
4h 15m
Nonstop
12:15 pmMDW
Southwest Airlines
10:00 amMDW
4h 50m
Nonstop
12:50 pmSFO

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, Feb 6 – Sat, Feb 13

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

Sat, Feb 6 – Sat, Feb 13

Southwest Airlines
1:05 pmSFO
7h 55m
STL · 2h 55m
11:00 pmMDW
Southwest Airlines
10:00 amMDW
4h 50m
Nonstop
12:50 pmSFO

Round-trip total · 1 adult · Taxes included

Sat, Feb 6 – Sat, Feb 13

Southwest Airlines
8:20 amSFO
6h 55m
LAX · 1h 25m
5:15 pmMDW
Southwest Airlines
10:00 amMDW
4h 50m
Nonstop
12:50 pmSFO

Round-trip total · 1 adult · Taxes included

Sat, Feb 6 – Sat, Feb 13

Southwest Airlines
8:20 pmSFO
7h 25m
PHX · 2h
5:45 am+1MDW
Southwest Airlines
10:00 amMDW
4h 50m
Nonstop
12:50 pmSFO

Round-trip total · 1 adult · Taxes included

Sat, Feb 6 – Sat, Feb 13

Southwest Airlines
8:00 amSFO
7h 55m
DEN · 3h 10m
5:55 pmMDW
Southwest Airlines
10:00 amMDW
4h 50m
Nonstop
12:50 pmSFO

Round-trip total · 1 adult · Taxes included

Sat, Feb 6 – Sat, Feb 13

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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Explore this route

All dates for this routeFeb 5, 2027 → Feb 12, 2027Feb 7, 2027 → Feb 14, 2027
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.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: San Francisco Bay Area to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-02-06 → 2027-02-13Southwest AirlinesWN3849 / WN3288$348.252026-10-29T01:18:59Z
2027-02-06 → 2027-02-13Delta Air LinesDL570 + DL1728 / DL4688 + DL442$388.052026-10-29T01:18:59Z
2027-02-06 → 2027-02-13Southwest AirlinesWN2331 / WN3288$348.252026-10-29T01:18:59Z
2027-02-06 → 2027-02-13Southwest AirlinesWN2989 + WN4770 / WN3288$329.252026-10-29T01:18:59Z
2027-02-06 → 2027-02-13Southwest AirlinesWN3847 + WN2515 / WN3288$329.252026-10-29T01:18:59Z
2027-02-06 → 2027-02-13Southwest AirlinesWN2749 + WN4963 / WN3288$329.252026-10-29T01:18:59Z
2027-02-06 → 2027-02-13Southwest AirlinesWN3428 + WN1699 / WN3288$329.252026-10-29T01:18:59Z
2027-02-06 → 2027-02-13Delta Air LinesDL2178 + DL4714 / DL4688 + DL442$388.052026-10-29T01:18:59Z

2027-02-06 → 2027-02-13 · $348.25

  • Southwest Airlines WN3849: SFO 2027-02-06 23:35:00 → MDW 2027-02-07 06:00:00; nonstop; 265 minutes. Local airport times.
  • Southwest Airlines WN3288: MDW 2027-02-13 10:00:00 → SFO 2027-02-13 12:50:00; nonstop; 290 minutes. Local airport times.

2027-02-06 → 2027-02-13 · $388.05

  • Delta Air Lines DL570 / DL1728: SFO 2027-02-06 06:00:00 → MDW 2027-02-06 16:18:00; 1 stop(s) via ATL; 498 minutes. Local airport times.
    • DL570: SFO 2027-02-06 06:00:00 → ATL 2027-02-06 13:29:00; layover at ATL: 116 minutes.
    • DL1728: ATL 2027-02-06 15:25:00 → MDW 2027-02-06 16:18:00.
  • Delta Air Lines DL4688 / DL442: MDW 2027-02-13 13:31:00 → SFO 2027-02-13 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2027-02-13 13:31:00 → DTW 2027-02-13 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2027-02-13 16:59:00 → SFO 2027-02-13 19:16:00.

2027-02-06 → 2027-02-13 · $348.25

  • Southwest Airlines WN2331: SFO 2027-02-06 06:00:00 → MDW 2027-02-06 12:15:00; nonstop; 255 minutes. Local airport times.
  • Southwest Airlines WN3288: MDW 2027-02-13 10:00:00 → SFO 2027-02-13 12:50:00; nonstop; 290 minutes. Local airport times.

2027-02-06 → 2027-02-13 · $329.25

  • Southwest Airlines WN2989 / WN4770: SFO 2027-02-06 13:05:00 → MDW 2027-02-06 23:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
    • WN2989: SFO 2027-02-06 13:05:00 → STL 2027-02-06 18:55:00; layover at STL: 175 minutes.
    • WN4770: STL 2027-02-06 21:50:00 → MDW 2027-02-06 23:00:00.
  • Southwest Airlines WN3288: MDW 2027-02-13 10:00:00 → SFO 2027-02-13 12:50:00; nonstop; 290 minutes. Local airport times.

2027-02-06 → 2027-02-13 · $329.25

  • Southwest Airlines WN3847 / WN2515: SFO 2027-02-06 08:20:00 → MDW 2027-02-06 17:15:00; 1 stop(s) via LAX; 415 minutes. Local airport times.
    • WN3847: SFO 2027-02-06 08:20:00 → LAX 2027-02-06 09:50:00; layover at LAX: 85 minutes.
    • WN2515: LAX 2027-02-06 11:15:00 → MDW 2027-02-06 17:15:00.
  • Southwest Airlines WN3288: MDW 2027-02-13 10:00:00 → SFO 2027-02-13 12:50:00; nonstop; 290 minutes. Local airport times.

2027-02-06 → 2027-02-13 · $329.25

  • Southwest Airlines WN2749 / WN4963: SFO 2027-02-06 20:20:00 → MDW 2027-02-07 05:45:00; 1 stop(s) via PHX; 445 minutes. Local airport times.
    • WN2749: SFO 2027-02-06 20:20:00 → PHX 2027-02-06 23:35:00; layover at PHX: 120 minutes.
    • WN4963: PHX 2027-02-07 01:35:00 → MDW 2027-02-07 05:45:00.
  • Southwest Airlines WN3288: MDW 2027-02-13 10:00:00 → SFO 2027-02-13 12:50:00; nonstop; 290 minutes. Local airport times.

2027-02-06 → 2027-02-13 · $329.25

  • Southwest Airlines WN3428 / WN1699: SFO 2027-02-06 08:00:00 → MDW 2027-02-06 17:55:00; 1 stop(s) via DEN; 475 minutes. Local airport times.
    • WN3428: SFO 2027-02-06 08:00:00 → DEN 2027-02-06 11:30:00; layover at DEN: 190 minutes.
    • WN1699: DEN 2027-02-06 14:40:00 → MDW 2027-02-06 17:55:00.
  • Southwest Airlines WN3288: MDW 2027-02-13 10:00:00 → SFO 2027-02-13 12:50:00; nonstop; 290 minutes. Local airport times.

2027-02-06 → 2027-02-13 · $388.05

  • Delta Air Lines DL2178 / DL4714: SFO 2027-02-06 06:00:00 → MDW 2027-02-06 16:39:00; 1 stop(s) via MSP; 519 minutes. Local airport times.
    • DL2178: SFO 2027-02-06 06:00:00 → MSP 2027-02-06 11:40:00; layover at MSP: 200 minutes.
    • DL4714: MSP 2027-02-06 15:00:00 → MDW 2027-02-06 16:39:00.
  • Delta Air Lines DL4688 / DL442: MDW 2027-02-13 13:31:00 → SFO 2027-02-13 19:16:00; 1 stop(s) via DTW; 465 minutes. Local airport times.
    • DL4688: MDW 2027-02-13 13:31:00 → DTW 2027-02-13 15:44:00; layover at DTW: 75 minutes.
    • DL442: DTW 2027-02-13 16:59:00 → SFO 2027-02-13 19:16:00.

Explore this route

For AI assistants

  • This page: San Francisco (SFO) to Chicago (MDW) · Feb 6, 2027 · return Feb 13, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.