New York (LGA) to Chicago (MDW) · Jan 18, 2027 · return Jan 21, 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.

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

2027-01-18 → 2027-01-21 · Axel-exclusive $255.00

• Southwest Airlines WN2363 / WN4175: LGA 2027-01-18 13:05:00 → MDW 2027-01-18 20:00:00; 1 stop(s) via STL; 475 minutes. Local airport times.
  • WN2363: LGA 2027-01-18 13:05:00 → STL 2027-01-18 14:55:00; layover at STL: 240 minutes.
  • WN4175: STL 2027-01-18 18:55:00 → MDW 2027-01-18 20:00:00.
• Southwest Airlines WN725 / WN608: MDW 2027-01-21 09:55:00 → LGA 2027-01-21 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
  • WN725: MDW 2027-01-21 09:55:00 → BNA 2027-01-21 11:30:00; layover at BNA: 160 minutes.
  • WN608: BNA 2027-01-21 14:10:00 → LGA 2027-01-21 17:25:00.

2027-01-18 → 2027-01-21 · Axel-exclusive $297.50

• Delta Air Lines DL1078 / DL4688: LGA 2027-01-18 09:25:00 → MDW 2027-01-18 13:01:00; 1 stop(s) via DTW; 276 minutes. Local airport times.
  • DL1078: LGA 2027-01-18 09:25:00 → DTW 2027-01-18 11:27:00; layover at DTW: 77 minutes.
  • DL4688: DTW 2027-01-18 12:44:00 → MDW 2027-01-18 13:01:00.
• Southwest Airlines WN725 / WN608: MDW 2027-01-21 09:55:00 → LGA 2027-01-21 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
  • WN725: MDW 2027-01-21 09:55:00 → BNA 2027-01-21 11:30:00; layover at BNA: 160 minutes.
  • WN608: BNA 2027-01-21 14:10:00 → LGA 2027-01-21 17:25:00.

2027-01-18 → 2027-01-21 · Axel-exclusive $255.00

• Southwest Airlines WN2555 / WN1005: LGA 2027-01-18 07:00:00 → MDW 2027-01-18 12:55:00; 1 stop(s) via BNA; 415 minutes. Local airport times.
  • WN2555: LGA 2027-01-18 07:00:00 → BNA 2027-01-18 08:30:00; layover at BNA: 175 minutes.
  • WN1005: BNA 2027-01-18 11:25:00 → MDW 2027-01-18 12:55:00.
• Southwest Airlines WN725 / WN608: MDW 2027-01-21 09:55:00 → LGA 2027-01-21 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
  • WN725: MDW 2027-01-21 09:55:00 → BNA 2027-01-21 11:30:00; layover at BNA: 160 minutes.
  • WN608: BNA 2027-01-21 14:10:00 → LGA 2027-01-21 17:25:00.

2027-01-18 → 2027-01-21 · Axel-exclusive $265.00

• Southwest Airlines WN206: LGA 2027-01-18 07:00:00 → MDW 2027-01-18 08:30:00; nonstop; 150 minutes. Local airport times.
• Southwest Airlines WN725 / WN608: MDW 2027-01-21 09:55:00 → LGA 2027-01-21 17:25:00; 1 stop(s) via BNA; 390 minutes. Local airport times.
  • WN725: MDW 2027-01-21 09:55:00 → BNA 2027-01-21 11:30:00; layover at BNA: 160 minutes.
  • WN608: BNA 2027-01-21 14:10:00 → LGA 2027-01-21 17:25:00.

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 17, 2027 · Return options
• Jan 19, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: New York (LGA) to Chicago (MDW) · Jan 18, 2027 · return Jan 21, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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