San Diego (SAN) to Chicago (MDW) · Jan 2, 2027 · return Jan 10, 2027

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.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Jan 2–10, 2027 · 8 nights · 2 adults, 1 room): 3★ The Willows Hotel, $827 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $931 total · 5★ Nobu Hotel Chicago, $2,840 total

All hotels in Chicago

Route overview: San Diego to Chicago (MDW) flight deals

2027-01-02 → 2027-01-10 · Axel-exclusive $404.71

• Southwest Airlines WN634: SAN 2027-01-02 08:15:00 → MDW 2027-01-02 14:15:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN1987: MDW 2027-01-10 21:15:00 → SAN 2027-01-10 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-10 · Axel-exclusive $404.71

• Southwest Airlines WN2962: SAN 2027-01-02 16:05:00 → MDW 2027-01-02 22:00:00; nonstop; 235 minutes. Local airport times.
• Southwest Airlines WN1987: MDW 2027-01-10 21:15:00 → SAN 2027-01-10 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-10 · Axel-exclusive $384.76

• Southwest Airlines WN3681 / WN295: SAN 2027-01-02 08:10:00 → MDW 2027-01-02 17:20:00; 1 stop(s) via AUS; 430 minutes. Local airport times.
  • WN3681: SAN 2027-01-02 08:10:00 → AUS 2027-01-02 13:00:00; layover at AUS: 110 minutes.
  • WN295: AUS 2027-01-02 14:50:00 → MDW 2027-01-02 17:20:00.
• Southwest Airlines WN1987: MDW 2027-01-10 21:15:00 → SAN 2027-01-10 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-10 · Axel-exclusive $384.76

• Southwest Airlines WN3752 / WN4349: SAN 2027-01-02 08:25:00 → MDW 2027-01-02 16:45:00; 1 stop(s) via SLC; 380 minutes. Local airport times.
  • WN3752: SAN 2027-01-02 08:25:00 → SLC 2027-01-02 11:35:00; layover at SLC: 70 minutes.
  • WN4349: SLC 2027-01-02 12:45:00 → MDW 2027-01-02 16:45:00.
• Southwest Airlines WN1987: MDW 2027-01-10 21:15:00 → SAN 2027-01-10 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-10 · Axel-exclusive $384.76

• Southwest Airlines WN4711 / WN4175: SAN 2027-01-02 11:55:00 → MDW 2027-01-02 20:00:00; 1 stop(s) via STL; 365 minutes. Local airport times.
  • WN4711: SAN 2027-01-02 11:55:00 → STL 2027-01-02 17:25:00; layover at STL: 90 minutes.
  • WN4175: STL 2027-01-02 18:55:00 → MDW 2027-01-02 20:00:00.
• Southwest Airlines WN1987: MDW 2027-01-10 21:15:00 → SAN 2027-01-10 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-10 · Axel-exclusive $384.76

• Southwest Airlines WN3699 / WN776: SAN 2027-01-02 12:30:00 → MDW 2027-01-02 21:30:00; 1 stop(s) via DEN; 420 minutes. Local airport times.
  • WN3699: SAN 2027-01-02 12:30:00 → DEN 2027-01-02 15:50:00; layover at DEN: 135 minutes.
  • WN776: DEN 2027-01-02 18:05:00 → MDW 2027-01-02 21:30:00.
• Southwest Airlines WN1987: MDW 2027-01-10 21:15:00 → SAN 2027-01-10 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-10 · Axel-exclusive $384.76

• Southwest Airlines WN4669 / WN651: SAN 2027-01-02 11:55:00 → MDW 2027-01-02 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
  • WN4669: SAN 2027-01-02 11:55:00 → BNA 2027-01-02 17:45:00; layover at BNA: 105 minutes.
  • WN651: BNA 2027-01-02 19:30:00 → MDW 2027-01-02 21:05:00.
• Southwest Airlines WN1987: MDW 2027-01-10 21:15:00 → SAN 2027-01-10 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-02 → 2027-01-10 · Axel-exclusive $384.76

• Southwest Airlines WN399 / WN1407: SAN 2027-01-02 12:10:00 → MDW 2027-01-02 19:45:00; 1 stop(s) via OMA; 335 minutes. Local airport times.
  • WN399: SAN 2027-01-02 12:10:00 → OMA 2027-01-02 17:15:00; layover at OMA: 65 minutes.
  • WN1407: OMA 2027-01-02 18:20:00 → MDW 2027-01-02 19:45:00.
• Southwest Airlines WN1987: MDW 2027-01-10 21:15:00 → SAN 2027-01-10 23:55:00; nonstop; 280 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 1, 2027 · Return options
• Jan 3, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: San Diego (SAN) to Chicago (MDW) · Jan 2, 2027 · return Jan 10, 2027: 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: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• 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.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel San Diego to Chicago (MDW) flight deals · Flight search guide.
• 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. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. 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.

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