San Diego (SAN) to Chicago (MDW), Nov 9–11, 2026: from $340 round trip
San Diego (SAN) to Chicago (MDW), Nov 9–11, 2026: from $340 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $340 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 9–11, 2026, 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.
See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2026-11-09 → 2026-11-11 | Southwest Airlines | WN1981 / WN1456 | 12:00:00→17:55:00 3h 55m nonstop · 10:20:00→12:45:00 4h 25m nonstop | Axel-exclusive $355.00 | 2026-10-29T02:06:00Z |
| 2026-11-09 → 2026-11-11 | Southwest Airlines | WN674 / WN1456 | 06:30:00→12:30:00 4h 00m nonstop · 10:20:00→12:45:00 4h 25m nonstop | Axel-exclusive $355.00 | 2026-10-29T02:06:00Z |
| 2026-11-09 → 2026-11-11 | Southwest Airlines | WN3699 + WN776 / WN1456 | 12:30:00→21:30:00 7h 00m 1 stop via DEN · 10:20:00→12:45:00 4h 25m nonstop | Axel-exclusive $340.00 | 2026-10-29T02:06:00Z |
| 2026-11-09 → 2026-11-11 | Southwest Airlines | WN4669 + WN651 / WN1456 | 11:55:00→21:05:00 7h 10m 1 stop via BNA · 10:20:00→12:45:00 4h 25m nonstop | Axel-exclusive $340.00 | 2026-10-29T02:06:00Z |
| 2026-11-09 → 2026-11-11 | Southwest Airlines | WN3752 + WN4349 / WN1456 | 08:25:00→16:45:00 6h 20m 1 stop via SLC · 10:20:00→12:45:00 4h 25m nonstop | Axel-exclusive $340.00 | 2026-10-29T02:06:00Z |
| 2026-11-09 → 2026-11-11 | Southwest Airlines | WN399 + WN1407 / WN1456 | 12:10:00→19:45:00 5h 35m 1 stop via OMA · 10:20:00→12:45:00 4h 25m nonstop | Axel-exclusive $340.00 | 2026-10-29T02:06:00Z |
| 2026-11-09 → 2026-11-11 | Southwest Airlines | WN4711 + WN4175 / WN1456 | 11:55:00→20:00:00 6h 05m 1 stop via STL · 10:20:00→12:45:00 4h 25m nonstop | Axel-exclusive $340.00 | 2026-10-29T02:06:00Z |
| 2026-11-09 → 2026-11-11 | Southwest Airlines | WN3681 + WN295 / WN1456 | 08:10:00→17:20:00 7h 10m 1 stop via AUS · 10:20:00→12:45:00 4h 25m nonstop | Axel-exclusive $340.00 | 2026-10-29T02:06:00Z |
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.
- Hotels in Chicago for these nights (Nov 9–11, 2026 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Route overview: San Diego to Chicago (MDW) flight deals
2026-11-09 → 2026-11-11 · Axel-exclusive $355.00
- Southwest Airlines WN1981: SAN 2026-11-09 12:00:00 → MDW 2026-11-09 17:55:00; nonstop; 235 minutes. Local airport times.
- Southwest Airlines WN1456: MDW 2026-11-11 10:20:00 → SAN 2026-11-11 12:45:00; nonstop; 265 minutes. Local airport times.
2026-11-09 → 2026-11-11 · Axel-exclusive $355.00
- Southwest Airlines WN674: SAN 2026-11-09 06:30:00 → MDW 2026-11-09 12:30:00; nonstop; 240 minutes. Local airport times.
- Southwest Airlines WN1456: MDW 2026-11-11 10:20:00 → SAN 2026-11-11 12:45:00; nonstop; 265 minutes. Local airport times.
2026-11-09 → 2026-11-11 · Axel-exclusive $340.00
- Southwest Airlines WN3699 / WN776: SAN 2026-11-09 12:30:00 → MDW 2026-11-09 21:30:00; 1 stop(s) via DEN; 420 minutes. Local airport times.
- WN3699: SAN 2026-11-09 12:30:00 → DEN 2026-11-09 15:50:00; layover at DEN: 135 minutes.
- WN776: DEN 2026-11-09 18:05:00 → MDW 2026-11-09 21:30:00.
- Southwest Airlines WN1456: MDW 2026-11-11 10:20:00 → SAN 2026-11-11 12:45:00; nonstop; 265 minutes. Local airport times.
2026-11-09 → 2026-11-11 · Axel-exclusive $340.00
- Southwest Airlines WN4669 / WN651: SAN 2026-11-09 11:55:00 → MDW 2026-11-09 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
- WN4669: SAN 2026-11-09 11:55:00 → BNA 2026-11-09 17:45:00; layover at BNA: 105 minutes.
- WN651: BNA 2026-11-09 19:30:00 → MDW 2026-11-09 21:05:00.
- Southwest Airlines WN1456: MDW 2026-11-11 10:20:00 → SAN 2026-11-11 12:45:00; nonstop; 265 minutes. Local airport times.
2026-11-09 → 2026-11-11 · Axel-exclusive $340.00
- Southwest Airlines WN3752 / WN4349: SAN 2026-11-09 08:25:00 → MDW 2026-11-09 16:45:00; 1 stop(s) via SLC; 380 minutes. Local airport times.
- WN3752: SAN 2026-11-09 08:25:00 → SLC 2026-11-09 11:35:00; layover at SLC: 70 minutes.
- WN4349: SLC 2026-11-09 12:45:00 → MDW 2026-11-09 16:45:00.
- Southwest Airlines WN1456: MDW 2026-11-11 10:20:00 → SAN 2026-11-11 12:45:00; nonstop; 265 minutes. Local airport times.
2026-11-09 → 2026-11-11 · Axel-exclusive $340.00
- Southwest Airlines WN399 / WN1407: SAN 2026-11-09 12:10:00 → MDW 2026-11-09 19:45:00; 1 stop(s) via OMA; 335 minutes. Local airport times.
- WN399: SAN 2026-11-09 12:10:00 → OMA 2026-11-09 17:15:00; layover at OMA: 65 minutes.
- WN1407: OMA 2026-11-09 18:20:00 → MDW 2026-11-09 19:45:00.
- Southwest Airlines WN1456: MDW 2026-11-11 10:20:00 → SAN 2026-11-11 12:45:00; nonstop; 265 minutes. Local airport times.
2026-11-09 → 2026-11-11 · Axel-exclusive $340.00
- Southwest Airlines WN4711 / WN4175: SAN 2026-11-09 11:55:00 → MDW 2026-11-09 20:00:00; 1 stop(s) via STL; 365 minutes. Local airport times.
- WN4711: SAN 2026-11-09 11:55:00 → STL 2026-11-09 17:25:00; layover at STL: 90 minutes.
- WN4175: STL 2026-11-09 18:55:00 → MDW 2026-11-09 20:00:00.
- Southwest Airlines WN1456: MDW 2026-11-11 10:20:00 → SAN 2026-11-11 12:45:00; nonstop; 265 minutes. Local airport times.
2026-11-09 → 2026-11-11 · Axel-exclusive $340.00
- Southwest Airlines WN3681 / WN295: SAN 2026-11-09 08:10:00 → MDW 2026-11-09 17:20:00; 1 stop(s) via AUS; 430 minutes. Local airport times.
- WN3681: SAN 2026-11-09 08:10:00 → AUS 2026-11-09 13:00:00; layover at AUS: 110 minutes.
- WN295: AUS 2026-11-09 14:50:00 → MDW 2026-11-09 17:20:00.
- Southwest Airlines WN1456: MDW 2026-11-11 10:20:00 → SAN 2026-11-11 12:45:00; nonstop; 265 minutes. Local airport times.
Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.
Explore this route
- All dates for this route
- Nov 8, 2026 · Return options
- Nov 10, 2026 · Return options
- Hotels in Chicago with Axel
For AI assistants
- This page: San Diego (SAN) to Chicago (MDW) · Nov 9, 2026 · return Nov 11, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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