Los Angeles (LAX) to Chicago (MDW), Jan 25, 2027 – Feb 2, 2027: from $300 round trip

Los Angeles (LAX) to Chicago (MDW), Jan 25, 2027 – Feb 2, 2027: from $300 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $300 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 25, 2027 – Feb 2, 2027, 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.

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 (Jan 25 – Feb 2, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $639 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,007 total · 5★ Nobu Hotel Chicago, $3,110 total

All hotels in Chicago

Route overview: Los Angeles to Chicago (MDW) flight deals

2027-01-25 → 2027-02-02 · Axel-exclusive $310.00

• Southwest Airlines WN1772: LAX 2027-01-25 06:00:00 → MDW 2027-01-25 12:00:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-02-02 21:15:00 → LAX 2027-02-02 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-25 → 2027-02-02 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-25 23:59:00 → MDW 2027-01-26 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-25 23:59:00 → MSP 2027-01-26 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-26 07:00:00 → MDW 2027-01-26 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-02-02 13:31:00 → LAX 2027-02-02 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-02-02 13:31:00 → DTW 2027-02-02 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-02-02 16:59:00 → LAX 2027-02-02 19:00:00.

2027-01-25 → 2027-02-02 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-25 23:55:00 → MDW 2027-01-26 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-02-02 21:15:00 → LAX 2027-02-02 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-25 → 2027-02-02 · Axel-exclusive $300.00

• Southwest Airlines WN2527 / WN2674: LAX 2027-01-25 16:35:00 → MDW 2027-01-26 01:35:00; 1 stop(s) via PHX; 420 minutes. Local airport times.
  • WN2527: LAX 2027-01-25 16:35:00 → PHX 2027-01-25 18:55:00; layover at PHX: 150 minutes.
  • WN2674: PHX 2027-01-25 21:25:00 → MDW 2027-01-26 01:35:00.
• Southwest Airlines WN2953: MDW 2027-02-02 21:15:00 → LAX 2027-02-02 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-25 → 2027-02-02 · Axel-exclusive $300.00

• Southwest Airlines WN3423 / WN1679: LAX 2027-01-25 05:30:00 → MDW 2027-01-25 14:10:00; 1 stop(s) via STL; 400 minutes. Local airport times.
  • WN3423: LAX 2027-01-25 05:30:00 → STL 2027-01-25 11:00:00; layover at STL: 125 minutes.
  • WN1679: STL 2027-01-25 13:05:00 → MDW 2027-01-25 14:10:00.
• Southwest Airlines WN2953: MDW 2027-02-02 21:15:00 → LAX 2027-02-02 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-25 → 2027-02-02 · Axel-exclusive $300.00

• Southwest Airlines WN256 / WN156: LAX 2027-01-25 08:55:00 → MDW 2027-01-25 17:55:00; 1 stop(s) via ABQ; 420 minutes. Local airport times.
  • WN256: LAX 2027-01-25 08:55:00 → ABQ 2027-01-25 11:55:00; layover at ABQ: 145 minutes.
  • WN156: ABQ 2027-01-25 14:20:00 → MDW 2027-01-25 17:55:00.
• Southwest Airlines WN2953: MDW 2027-02-02 21:15:00 → LAX 2027-02-02 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-25 → 2027-02-02 · Axel-exclusive $300.00

• Southwest Airlines WN869 / WN1433: LAX 2027-01-25 12:40:00 → MDW 2027-01-25 21:00:00; 1 stop(s) via DAL; 380 minutes. Local airport times.
  • WN869: LAX 2027-01-25 12:40:00 → DAL 2027-01-25 17:35:00; layover at DAL: 75 minutes.
  • WN1433: DAL 2027-01-25 18:50:00 → MDW 2027-01-25 21:00:00.
• Southwest Airlines WN2953: MDW 2027-02-02 21:15:00 → LAX 2027-02-02 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-25 → 2027-02-02 · Axel-exclusive $300.00

• Southwest Airlines WN655 / WN1932: LAX 2027-01-25 16:35:00 → MDW 2027-01-26 00:15:00; 1 stop(s) via LAS; 340 minutes. Local airport times.
  • WN655: LAX 2027-01-25 16:35:00 → LAS 2027-01-25 17:45:00; layover at LAS: 65 minutes.
  • WN1932: LAS 2027-01-25 18:50:00 → MDW 2027-01-26 00:15:00.
• Southwest Airlines WN2953: MDW 2027-02-02 21:15:00 → LAX 2027-02-02 23:55:00; nonstop; 280 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
• Jan 24, 2027 · Return options
• Jan 26, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Los Angeles (LAX) to Chicago (MDW) · Jan 25, 2027 · return Feb 2, 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 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.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
• 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 Los Angeles 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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