New York (JFK) to Chicago (MDW), Jan 21, 2027: round trips from $328, one way from $176

New York (JFK) to Chicago (MDW), Jan 21, 2027: round trips from $328, one way from $176 on Axel, checked Oct 29, 2026. Lowest published fares: $328 round trip, Axel-exclusive, Delta Air Lines, 1 stop, Jan 21–22, 2027; $176 one way, Axel-exclusive, Delta Air Lines, 1 stop, Jan 21, 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 21–22, 2027 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21–23, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21–25, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21–26, 2027 · 5 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21–27, 2027 · 6 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21–28, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21–29, 2027 · 8 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21–30, 2027 · 9 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21–31, 2027 · 10 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21 – Feb 1, 2027 · 11 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21 – Feb 2, 2027 · 12 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21 – Feb 3, 2027 · 13 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
• Hotels in Chicago for these nights (Jan 21 – Feb 4, 2027 · 14 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

All hotels in Chicago

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

2027-01-21 · one way · Axel-exclusive $175.75

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.

2027-01-21 → 2027-01-22 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-01-22 13:31:00 → JFK 2027-01-22 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-01-22 13:31:00 → DTW 2027-01-22 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-01-22 18:32:00 → JFK 2027-01-22 20:39:00.

2027-01-21 → 2027-01-23 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-01-23 13:31:00 → JFK 2027-01-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-01-23 13:31:00 → DTW 2027-01-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-01-23 18:32:00 → JFK 2027-01-23 20:39:00.

2027-01-21 → 2027-01-24 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-01-24 13:31:00 → JFK 2027-01-24 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-01-24 13:31:00 → DTW 2027-01-24 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-01-24 18:32:00 → JFK 2027-01-24 20:39:00.

2027-01-21 → 2027-01-25 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-01-25 13:31:00 → JFK 2027-01-25 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-01-25 13:31:00 → DTW 2027-01-25 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-01-25 18:32:00 → JFK 2027-01-25 20:39:00.

2027-01-21 → 2027-01-27 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-01-27 13:31:00 → JFK 2027-01-27 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-01-27 13:31:00 → DTW 2027-01-27 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-01-27 18:32:00 → JFK 2027-01-27 20:39:00.

2027-01-21 → 2027-01-28 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-01-28 13:31:00 → JFK 2027-01-28 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-01-28 13:31:00 → DTW 2027-01-28 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-01-28 18:32:00 → JFK 2027-01-28 20:39:00.

2027-01-21 → 2027-01-29 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-01-29 13:31:00 → JFK 2027-01-29 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-01-29 13:31:00 → DTW 2027-01-29 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-01-29 18:32:00 → JFK 2027-01-29 20:39:00.

2027-01-21 → 2027-01-31 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-01-31 13:31:00 → JFK 2027-01-31 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-01-31 13:31:00 → DTW 2027-01-31 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-01-31 18:32:00 → JFK 2027-01-31 20:39:00.

2027-01-21 → 2027-02-01 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-02-01 13:31:00 → JFK 2027-02-01 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-02-01 13:31:00 → DTW 2027-02-01 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-02-01 18:32:00 → JFK 2027-02-01 20:39:00.

2027-01-21 → 2027-02-02 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-02-02 13:31:00 → JFK 2027-02-02 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-02-02 13:31:00 → DTW 2027-02-02 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-02-02 18:32:00 → JFK 2027-02-02 20:39:00.

2027-01-21 → 2027-02-04 · Axel-exclusive $327.76

• Delta Air Lines DL2751 / DL4677: JFK 2027-01-21 12:59:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-21 12:59:00 → DTW 2027-01-21 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
• Delta Air Lines DL4688 / DL5045: MDW 2027-02-04 13:31:00 → JFK 2027-02-04 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-02-04 13:31:00 → DTW 2027-02-04 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-02-04 18:32:00 → JFK 2027-02-04 20:39:00.

Explore this route

• All dates for this route
• Jan 20, 2027 · Return options
• Jan 22, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: New York (JFK) to Chicago (MDW) · Jan 21, 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.
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