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Route overview: New York to Chicago (MDW) flight deals

New York (LGA) to Chicago (MDW), Nov 7–21, 2026: from $265 round trip

New York (LGA) to Chicago (MDW), Nov 7–21, 2026: from $265 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $265 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 7–21, 2026, 1 adult, economy, checked Oct 29, 2026.

LGA → MDW1 adulteconomyRound trip

5 flight options · 2 airlines

Nonstop flights

Sat, Nov 7 – Sat, Nov 21

Southwest Airlines
7:00 amLGA
2h 30m
Nonstop
8:30 amMDW
Southwest Airlines
8:05 amMDW
2h 10m
Nonstop
11:15 amLGA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sat, Nov 21

Southwest Airlines
3:00 pmLGA
2h 35m
Nonstop
4:35 pmMDW
Southwest Airlines
8:05 amMDW
2h 10m
Nonstop
11:15 amLGA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sat, Nov 7 – Sat, Nov 21

Delta Air Lines
9:25 amLGA
4h 36m
DTW · 1h 17m
1:01 pmMDW
Southwest Airlines
8:05 amMDW
2h 10m
Nonstop
11:15 amLGA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sat, Nov 21

Southwest Airlines
1:05 pmLGA
7h 55m
STL · 4h
8:00 pmMDW
Southwest Airlines
8:05 amMDW
2h 10m
Nonstop
11:15 amLGA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 7 – Sat, Nov 21

Southwest Airlines
7:00 amLGA
6h 55m
BNA · 2h 55m
12:55 pmMDW
Southwest Airlines
8:05 amMDW
2h 10m
Nonstop
11:15 amLGA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Nov 7–21, 2026 · 14 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

Make this trip yours

LGA ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

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All dates for this routeNov 8, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

New York (LGA) to Chicago (MDW), Nov 7–21, 2026: from $265 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $265 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 7–21, 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 datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2026-11-07 → 2026-11-21Southwest AirlinesWN206 / WN267907:00:00→08:30:00 2h 30m nonstop · 08:05:00→11:15:00 2h 10m nonstopAxel-exclusive $275.002026-10-29T01:26:39Z
2026-11-07 → 2026-11-21Delta Air Lines / Southwest AirlinesDL1078 + DL4688 / WN267909:25:00→13:01:00 4h 36m 1 stop via DTW · 08:05:00→11:15:00 2h 10m nonstopAxel-exclusive $307.502026-10-29T01:26:39Z
2026-11-07 → 2026-11-21Southwest AirlinesWN4234 / WN267915:00:00→16:35:00 2h 35m nonstop · 08:05:00→11:15:00 2h 10m nonstopAxel-exclusive $275.002026-10-29T01:26:39Z
2026-11-07 → 2026-11-21Southwest AirlinesWN2363 + WN4175 / WN267913:05:00→20:00:00 7h 55m 1 stop via STL · 08:05:00→11:15:00 2h 10m nonstopAxel-exclusive $265.002026-10-29T01:26:39Z
2026-11-07 → 2026-11-21Southwest AirlinesWN2555 + WN1005 / WN267907:00:00→12:55:00 6h 55m 1 stop via BNA · 08:05:00→11:15:00 2h 10m nonstopAxel-exclusive $265.002026-10-29T01:26:39Z

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.

All hotels in Chicago

Route overview: New York to Chicago (MDW) flight deals

2026-11-07 → 2026-11-21 · Axel-exclusive $275.00

  • Southwest Airlines WN206: LGA 2026-11-07 07:00:00 → MDW 2026-11-07 08:30:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2679: MDW 2026-11-21 08:05:00 → LGA 2026-11-21 11:15:00; nonstop; 130 minutes. Local airport times.

2026-11-07 → 2026-11-21 · Axel-exclusive $307.50

  • Delta Air Lines DL1078 / DL4688: LGA 2026-11-07 09:25:00 → MDW 2026-11-07 13:01:00; 1 stop(s) via DTW; 276 minutes. Local airport times.
    • DL1078: LGA 2026-11-07 09:25:00 → DTW 2026-11-07 11:27:00; layover at DTW: 77 minutes.
    • DL4688: DTW 2026-11-07 12:44:00 → MDW 2026-11-07 13:01:00.
  • Southwest Airlines WN2679: MDW 2026-11-21 08:05:00 → LGA 2026-11-21 11:15:00; nonstop; 130 minutes. Local airport times.

2026-11-07 → 2026-11-21 · Axel-exclusive $275.00

  • Southwest Airlines WN4234: LGA 2026-11-07 15:00:00 → MDW 2026-11-07 16:35:00; nonstop; 155 minutes. Local airport times.
  • Southwest Airlines WN2679: MDW 2026-11-21 08:05:00 → LGA 2026-11-21 11:15:00; nonstop; 130 minutes. Local airport times.

2026-11-07 → 2026-11-21 · Axel-exclusive $265.00

  • Southwest Airlines WN2363 / WN4175: LGA 2026-11-07 13:05:00 → MDW 2026-11-07 20:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
    • WN2363: LGA 2026-11-07 13:05:00 → STL 2026-11-07 14:55:00; layover at STL: 240 minutes.
    • WN4175: STL 2026-11-07 18:55:00 → MDW 2026-11-07 20:00:00.
  • Southwest Airlines WN2679: MDW 2026-11-21 08:05:00 → LGA 2026-11-21 11:15:00; nonstop; 130 minutes. Local airport times.

2026-11-07 → 2026-11-21 · Axel-exclusive $265.00

  • Southwest Airlines WN2555 / WN1005: LGA 2026-11-07 07:00:00 → MDW 2026-11-07 12:55:00; 1 stop(s) via BNA; 415 minutes. Local airport times.
    • WN2555: LGA 2026-11-07 07:00:00 → BNA 2026-11-07 08:30:00; layover at BNA: 175 minutes.
    • WN1005: BNA 2026-11-07 11:25:00 → MDW 2026-11-07 12:55:00.
  • Southwest Airlines WN2679: MDW 2026-11-21 08:05:00 → LGA 2026-11-21 11:15:00; nonstop; 130 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.

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For AI assistants

  • This page: New York (LGA) to Chicago (MDW) · Nov 7, 2026 · return Nov 21, 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.
  • 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 New York 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.