Los Angeles (LAX) to Chicago (MDW), Jan 29, 2027: round trips from $310, one way from $165

Los Angeles (LAX) to Chicago (MDW), Jan 29, 2027: round trips from $310, one way from $165 on Axel, checked Oct 29, 2026. Lowest published fares: $310 round trip, Axel-exclusive, Southwest Airlines, nonstop, Jan 29–30, 2027; $165 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 29, 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

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 29–30, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $84 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $95 total · 5★ Sofitel Chicago Magnificent Mile, $258 total
• Hotels in Chicago for these nights (Jan 29–31, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $159 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $198 total · 5★ Sofitel Chicago Magnificent Mile, $516 total
• Hotels in Chicago for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $242 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $286 total · 5★ Sofitel Chicago Magnificent Mile, $778 total
• Hotels in Chicago for these nights (Jan 29 – Feb 2, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $331 total · 4★ Warwick Allerton - Chicago, $384 total · 5★ Sofitel Chicago Magnificent Mile, $1,036 total
• Hotels in Chicago for these nights (Jan 29 – Feb 3, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $420 total · 4★ Warwick Allerton - Chicago, $478 total · 5★ Sofitel Chicago Magnificent Mile, $1,298 total
• Hotels in Chicago for these nights (Jan 29 – Feb 4, 2027 · 6 nights · 2 adults, 1 room): 3★ Hotel Versey, $506 total · 4★ Warwick Allerton - Chicago, $567 total · 5★ Sofitel Chicago Magnificent Mile, $1,560 total
• Hotels in Chicago for these nights (Jan 29 – Feb 5, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $580 total · 4★ Warwick Allerton - Chicago, $653 total · 5★ Sofitel Chicago Magnificent Mile, $1,822 total
• Hotels in Chicago for these nights (Jan 29 – Feb 6, 2027 · 8 nights · 2 adults, 1 room): 3★ Hotel Versey, $682 total · 4★ Warwick Allerton - Chicago, $745 total · 5★ Sofitel Chicago Magnificent Mile, $2,086 total
• Hotels in Chicago for these nights (Jan 29 – Feb 7, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $786 total · 4★ Warwick Allerton - Chicago, $834 total · 5★ Sofitel Chicago Magnificent Mile, $2,348 total
• Hotels in Chicago for these nights (Jan 29 – Feb 8, 2027 · 10 nights · 2 adults, 1 room): 3★ Hotel Versey, $878 total · 4★ Warwick Allerton - Chicago, $926 total · 5★ Sofitel Chicago Magnificent Mile, $2,621 total
• Hotels in Chicago for these nights (Jan 29 – Feb 9, 2027 · 11 nights · 2 adults, 1 room): 3★ Hotel Versey, $961 total · 4★ Warwick Allerton - Chicago, $1,012 total · 5★ Sofitel Chicago Magnificent Mile, $2,883 total
• Hotels in Chicago for these nights (Jan 29 – Feb 10, 2027 · 12 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,042 total · 4★ Warwick Allerton - Chicago, $1,108 total · 5★ Sofitel Chicago Magnificent Mile, $3,141 total
• Hotels in Chicago for these nights (Jan 29 – Feb 11, 2027 · 13 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,126 total · 4★ Warwick Allerton - Chicago, $1,208 total · 5★ Sofitel Chicago Magnificent Mile, $3,408 total
• Hotels in Chicago for these nights (Jan 29 – Feb 12, 2027 · 14 nights · 2 adults, 1 room): 3★ Hotel Versey, $1,209 total · 4★ Warwick Allerton - Chicago, $1,303 total · 5★ Sofitel Chicago Magnificent Mile, $3,666 total

All hotels in Chicago

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

2027-01-29 · one way · Axel-exclusive $165.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.

2027-01-29 · one way · Axel-exclusive $210.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.

2027-01-29 → 2027-01-30 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-01-30 18:25:00 → LAX 2027-01-30 21:00:00; nonstop; 275 minutes. Local airport times.

2027-01-29 → 2027-01-30 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-01-30 13:31:00 → LAX 2027-01-30 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-01-30 13:31:00 → DTW 2027-01-30 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-01-30 16:59:00 → LAX 2027-01-30 19:00:00.

2027-01-29 → 2027-01-31 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-01-31 21:45:00 → LAX 2027-02-01 00:15:00; nonstop; 270 minutes. Local airport times.

2027-01-29 → 2027-01-31 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-01-31 13:31:00 → LAX 2027-01-31 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-01-31 13:31:00 → DTW 2027-01-31 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-01-31 16:59:00 → LAX 2027-01-31 19:00:00.

2027-01-29 → 2027-02-01 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-02-01 21:45:00 → LAX 2027-02-02 00:15:00; nonstop; 270 minutes. Local airport times.

2027-01-29 → 2027-02-01 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-02-01 13:31:00 → LAX 2027-02-01 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-02-01 13:31:00 → DTW 2027-02-01 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-02-01 16:59:00 → LAX 2027-02-01 19:00:00.

2027-01-29 → 2027-02-02 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 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.

2027-01-29 → 2027-02-02 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 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.

2027-01-29 → 2027-02-04 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-02-04 21:15:00 → LAX 2027-02-04 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-29 → 2027-02-04 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-02-04 13:31:00 → LAX 2027-02-04 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-02-04 13:31:00 → DTW 2027-02-04 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-02-04 16:59:00 → LAX 2027-02-04 19:00:00.

2027-01-29 → 2027-02-05 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2950: MDW 2027-02-05 07:25:00 → LAX 2027-02-05 09:55:00; nonstop; 270 minutes. Local airport times.

2027-01-29 → 2027-02-05 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-02-05 13:31:00 → LAX 2027-02-05 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-02-05 13:31:00 → DTW 2027-02-05 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-02-05 16:59:00 → LAX 2027-02-05 19:00:00.

2027-01-29 → 2027-02-06 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-02-06 18:25:00 → LAX 2027-02-06 21:00:00; nonstop; 275 minutes. Local airport times.

2027-01-29 → 2027-02-06 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-02-06 13:31:00 → LAX 2027-02-06 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-02-06 13:31:00 → DTW 2027-02-06 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-02-06 16:59:00 → LAX 2027-02-06 19:00:00.

2027-01-29 → 2027-02-08 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-02-08 21:45:00 → LAX 2027-02-09 00:15:00; nonstop; 270 minutes. Local airport times.

2027-01-29 → 2027-02-08 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-02-08 13:31:00 → LAX 2027-02-08 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-02-08 13:31:00 → DTW 2027-02-08 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-02-08 16:59:00 → LAX 2027-02-08 19:00:00.

2027-01-29 → 2027-02-09 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-02-09 21:15:00 → LAX 2027-02-09 23:55:00; nonstop; 280 minutes. Local airport times.

2027-01-29 → 2027-02-09 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-02-09 13:31:00 → LAX 2027-02-09 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-02-09 13:31:00 → DTW 2027-02-09 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-02-09 16:59:00 → LAX 2027-02-09 19:00:00.

2027-01-29 → 2027-02-10 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2953: MDW 2027-02-10 21:45:00 → LAX 2027-02-11 00:15:00; nonstop; 270 minutes. Local airport times.

2027-01-29 → 2027-02-10 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-02-10 13:31:00 → LAX 2027-02-10 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-02-10 13:31:00 → DTW 2027-02-10 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-02-10 16:59:00 → LAX 2027-02-10 19:00:00.

2027-01-29 → 2027-02-12 · Axel-exclusive $310.00

• Southwest Airlines WN2518: LAX 2027-01-29 23:55:00 → MDW 2027-01-30 05:55:00; nonstop; 240 minutes. Local airport times.
• Southwest Airlines WN2950: MDW 2027-02-12 07:25:00 → LAX 2027-02-12 09:55:00; nonstop; 270 minutes. Local airport times.

2027-01-29 → 2027-02-12 · Axel-exclusive $390.00

• Delta Air Lines DL430 / DL4712: LAX 2027-01-29 23:59:00 → MDW 2027-01-30 08:50:00; 1 stop(s) via MSP; 411 minutes. Local airport times.
  • DL430: LAX 2027-01-29 23:59:00 → MSP 2027-01-30 05:32:00; layover at MSP: 88 minutes.
  • DL4712: MSP 2027-01-30 07:00:00 → MDW 2027-01-30 08:50:00.
• Delta Air Lines DL4688 / DL883: MDW 2027-02-12 13:31:00 → LAX 2027-02-12 19:00:00; 1 stop(s) via DTW; 449 minutes. Local airport times.
  • DL4688: MDW 2027-02-12 13:31:00 → DTW 2027-02-12 15:44:00; layover at DTW: 75 minutes.
  • DL883: DTW 2027-02-12 16:59:00 → LAX 2027-02-12 19:00:00.

Explore this route

• All dates for this route
• Jan 28, 2027 · Return options
• Jan 30, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Los Angeles (LAX) to Chicago (MDW) · Jan 29, 2027 · choose your return date: 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 row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested 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.

Feedback (optional): Missing info · Axel issue