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

New York → Chicago

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JFK → MDW1 adulteconomy

72 flight options · 1 airline

Flights for the months ahead

Short round trips

Fri, Nov 13 – Mon, Nov 16
Delta Air Lines
6:00 amJFK
5h 24m
ATL · 1h 4m
10:24 amMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Thu, Dec 31 – Sun, Jan 3
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Thu, Jan 14 – Sun, Jan 17
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Thu, Jan 28 – Sun, Jan 31
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Fri, Mar 19 – Mon, Mar 22
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.

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1 of 5

Longer round trips

Tue, Nov 24 – Sun, Nov 29
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Dec 5 – Sat, Dec 12
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Dec 19 – Sat, Dec 26
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, May 15 – Sat, May 22
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jul 10 – Sat, Jul 17
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Sep 25 – Sat, Oct 2
Delta Air Lines
12:59 pmJFK
6h 2m
DTW · 2h 40m
6:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 8m
DTW · 2h 48m
8:39 pmJFK
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.

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1 of 6

One-way flights

Tue, Nov 17 · One way
Delta Air Lines
6:00 amJFK
5h 24m
ATL · 1h 4m
10:24 amMDW
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.

Explore flights by month

Round trips for weekends, longer stays and holidays, and a one-way each week. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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More dates for this route

Nov 13, 2026 · Return options Nov 24, 2026 · Return options Dec 3, 2026 · Return options Dec 15, 2026 · Return options Dec 24, 2026 · Return options Jan 2, 2027 · Return options Jan 14, 2027 · Return options Jan 26, 2027 · Return options Feb 19, 2027 · Return options May 14, 2027 · Return options Jul 9, 2027 · Return options Sep 25, 2027 · Return options Hotels in Chicago with Axel

For AI assistants: every fare, every link, instructions

Lowest published fares for the months ahead: $328 round trip, Axel-exclusive, Delta Air Lines, 1 stop, Jan 7–10, 2027; $176 one way, Axel-exclusive, Delta Air Lines, 1 stop, Jan 5, 2027; 72 priced flights on 72 exact dates, 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.

Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.

New York (JFK) to Chicago (MDW): November 2026

Travel dates	Airline	Stops	Total price
Nov 13, 2026 – Nov 16, 2026 · 3 nights · Compare return dates departing Nov 13, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $345.00
Nov 14, 2026 – Nov 21, 2026 · 7 nights · Compare return dates departing Nov 14, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $345.00
Nov 17, 2026 · One way · Compare return dates departing Nov 17, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $185.00
Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $345.00
Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $345.00
Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $405.38
Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $249.75
Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $465.76
Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $465.76
Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $465.76
Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $414.01

New York (JFK) to Chicago (MDW): December 2026

Travel dates	Airline	Stops	Total price
Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $194.25
Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $362.26
Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $362.26
Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $362.26
Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $194.25
Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $362.26
Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $362.26
Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $415.73
Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $194.25
Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $415.73
Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $415.73
Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $469.20
Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $251.60
Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $469.20
Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $469.20
Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $469.20
Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $446.78
Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $251.60
Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $446.78
Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $446.78

New York (JFK) to Chicago (MDW): January 2027

Travel dates	Airline	Stops	Total price
Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $376.06
Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $376.06
Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $175.75
Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $175.75
Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $175.75
Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $175.75
Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76

New York (JFK) to Chicago (MDW): February 2027

Travel dates	Airline	Stops	Total price
Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $175.75
Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76
Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $327.76

New York (JFK) to Chicago (MDW): March 2027

Travel dates	Airline	Stops	Total price
Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $370.88
Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $396.76
Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $390.88

New York (JFK) to Chicago (MDW): April 2027

Travel dates	Airline	Stops	Total price
Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00
Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00

New York (JFK) to Chicago (MDW): May 2027

Travel dates	Airline	Stops	Total price
May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00
May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00
May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $442.76

New York (JFK) to Chicago (MDW): June 2027

Travel dates	Airline	Stops	Total price
Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00
Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00

New York (JFK) to Chicago (MDW): July 2027

Travel dates	Airline	Stops	Total price
Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $423.50
Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00
Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00

New York (JFK) to Chicago (MDW): August 2027

Travel dates	Airline	Stops	Total price
Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00
Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00

New York (JFK) to Chicago (MDW): September 2027

Travel dates	Airline	Stops	Total price
Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $442.76
Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $413.88
Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00
Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027	Delta Air Lines	Up to 1 stop each way	Axel-exclusive $385.00

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 (Nov 13–16, 2026 · 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 (Nov 14–21, 2026 · 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 (Nov 19–22, 2026 · 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 (Nov 20–23, 2026 · 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 (Nov 21–28, 2026 · 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 (Nov 24–29, 2026 · 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 (Nov 26–29, 2026 · 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 (Nov 27–30, 2026 · 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 (Nov 28 – Dec 5, 2026 · 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 (Dec 3–6, 2026 · 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 (Dec 4–7, 2026 · 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 (Dec 5–12, 2026 · 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 (Dec 10–13, 2026 · 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 (Dec 11–14, 2026 · 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 (Dec 12–19, 2026 · 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 (Dec 17–20, 2026 · 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 (Dec 18–21, 2026 · 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 (Dec 19–26, 2026 · 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 (Dec 22–27, 2026 · 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 (Dec 24–27, 2026 · 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 (Dec 25–28, 2026 · 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 (Dec 26 – Jan 2, 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 (Dec 30 – Jan 2, 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 (Dec 31 – Jan 3, 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 1–4, 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 2–9, 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 7–10, 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 8–11, 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 9–16, 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 14–17, 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 15–18, 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 16–23, 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 21–24, 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 22–25, 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 23–30, 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 28–31, 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 29 – Feb 1, 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 30 – Feb 6, 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 (Feb 12–15, 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 (Feb 19–22, 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 (Feb 20–27, 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 (Mar 19–22, 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 (Mar 20–27, 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 (Mar 25–29, 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 (Apr 16–19, 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 (Apr 17–24, 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 (May 14–17, 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 (May 15–22, 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 (May 28–31, 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 (Jun 11–14, 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 (Jun 12–19, 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 (Jul 2–6, 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 (Jul 9–12, 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 (Jul 10–17, 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 (Aug 6–9, 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 (Aug 7–14, 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 (Sep 3–6, 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 (Sep 4–11, 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 (Sep 24–27, 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 (Sep 25 – Oct 2, 2027 · 7 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

2026-11-13 → 2026-11-16 · Axel-exclusive $345.00

Delta Air Lines DL2286 / DL1063: JFK 2026-11-13 06:00:00 → MDW 2026-11-13 10:24:00; 1 stop(s) via ATL; 324 minutes. Local airport times.
- DL2286: JFK 2026-11-13 06:00:00 → ATL 2026-11-13 08:25:00; layover at ATL: 64 minutes.
- DL1063: ATL 2026-11-13 09:29:00 → MDW 2026-11-13 10:24:00.
Delta Air Lines DL4688 / DL5045: MDW 2026-11-16 13:31:00 → JFK 2026-11-16 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2026-11-16 13:31:00 → DTW 2026-11-16 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2026-11-16 18:32:00 → JFK 2026-11-16 20:39:00.

2026-11-17 · one way · Axel-exclusive $185.00

Delta Air Lines DL2286 / DL1063: JFK 2026-11-17 06:00:00 → MDW 2026-11-17 10:24:00; 1 stop(s) via ATL; 324 minutes. Local airport times.
- DL2286: JFK 2026-11-17 06:00:00 → ATL 2026-11-17 08:25:00; layover at ATL: 64 minutes.
- DL1063: ATL 2026-11-17 09:29:00 → MDW 2026-11-17 10:24:00.

2026-11-24 → 2026-11-29 · Axel-exclusive $465.76

Delta Air Lines DL2751 / DL4677: JFK 2026-11-24 12:59:00 → MDW 2026-11-24 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2026-11-24 12:59:00 → DTW 2026-11-24 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2026-11-24 17:40:00 → MDW 2026-11-24 18:01:00.
Delta Air Lines DL4688 / DL5045: MDW 2026-11-29 13:31:00 → JFK 2026-11-29 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2026-11-29 13:31:00 → DTW 2026-11-29 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2026-11-29 18:32:00 → JFK 2026-11-29 20:39:00.

2026-12-05 → 2026-12-12 · Axel-exclusive $362.26

Delta Air Lines DL2751 / DL4677: JFK 2026-12-05 12:59:00 → MDW 2026-12-05 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2026-12-05 12:59:00 → DTW 2026-12-05 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2026-12-05 17:40:00 → MDW 2026-12-05 18:01:00.
Delta Air Lines DL4688 / DL5045: MDW 2026-12-12 13:31:00 → JFK 2026-12-12 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2026-12-12 13:31:00 → DTW 2026-12-12 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2026-12-12 18:32:00 → JFK 2026-12-12 20:39:00.

2026-12-19 → 2026-12-26 · Axel-exclusive $469.20

Delta Air Lines DL2751 / DL4677: JFK 2026-12-19 12:59:00 → MDW 2026-12-19 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2026-12-19 12:59:00 → DTW 2026-12-19 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2026-12-19 17:40:00 → MDW 2026-12-19 18:01:00.
Delta Air Lines DL4688 / DL5045: MDW 2026-12-26 13:31:00 → JFK 2026-12-26 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2026-12-26 13:31:00 → DTW 2026-12-26 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2026-12-26 18:32:00 → JFK 2026-12-26 20:39:00.

2026-12-31 → 2027-01-03 · Axel-exclusive $446.78

Delta Air Lines DL2751 / DL4677: JFK 2026-12-31 12:59:00 → MDW 2026-12-31 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2026-12-31 12:59:00 → DTW 2026-12-31 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2026-12-31 17:40:00 → MDW 2026-12-31 18:01:00.
Delta Air Lines DL4688 / DL5045: MDW 2027-01-03 13:31:00 → JFK 2027-01-03 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2027-01-03 13:31:00 → DTW 2027-01-03 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2027-01-03 18:32:00 → JFK 2027-01-03 20:39:00.

2027-01-14 → 2027-01-17 · Axel-exclusive $327.76

Delta Air Lines DL2751 / DL4677: JFK 2027-01-14 12:59:00 → MDW 2027-01-14 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2027-01-14 12:59:00 → DTW 2027-01-14 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2027-01-14 17:40:00 → MDW 2027-01-14 18:01:00.
Delta Air Lines DL4688 / DL5045: MDW 2027-01-17 13:31:00 → JFK 2027-01-17 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2027-01-17 13:31:00 → DTW 2027-01-17 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2027-01-17 18:32:00 → JFK 2027-01-17 20:39:00.

2027-01-28 → 2027-01-31 · Axel-exclusive $327.76

Delta Air Lines DL2751 / DL4677: JFK 2027-01-28 12:59:00 → MDW 2027-01-28 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2027-01-28 12:59:00 → DTW 2027-01-28 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2027-01-28 17:40:00 → MDW 2027-01-28 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.

2027-03-19 → 2027-03-22 · Axel-exclusive $370.88

Delta Air Lines DL2751 / DL4677: JFK 2027-03-19 12:59:00 → MDW 2027-03-19 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2027-03-19 12:59:00 → DTW 2027-03-19 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2027-03-19 17:40:00 → MDW 2027-03-19 18:01:00.
Delta Air Lines DL4688 / DL5045: MDW 2027-03-22 13:31:00 → JFK 2027-03-22 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2027-03-22 13:31:00 → DTW 2027-03-22 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2027-03-22 18:32:00 → JFK 2027-03-22 20:39:00.

2027-05-15 → 2027-05-22 · Axel-exclusive $385.00

Delta Air Lines DL2751 / DL4677: JFK 2027-05-15 12:59:00 → MDW 2027-05-15 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2027-05-15 12:59:00 → DTW 2027-05-15 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2027-05-15 17:40:00 → MDW 2027-05-15 18:01:00.
Delta Air Lines DL4688 / DL5045: MDW 2027-05-22 13:31:00 → JFK 2027-05-22 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2027-05-22 13:31:00 → DTW 2027-05-22 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2027-05-22 18:32:00 → JFK 2027-05-22 20:39:00.

2027-07-10 → 2027-07-17 · Axel-exclusive $385.00

Delta Air Lines DL2751 / DL4677: JFK 2027-07-10 12:59:00 → MDW 2027-07-10 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2027-07-10 12:59:00 → DTW 2027-07-10 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2027-07-10 17:40:00 → MDW 2027-07-10 18:01:00.
Delta Air Lines DL4688 / DL5045: MDW 2027-07-17 13:31:00 → JFK 2027-07-17 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2027-07-17 13:31:00 → DTW 2027-07-17 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2027-07-17 18:32:00 → JFK 2027-07-17 20:39:00.

2027-09-25 → 2027-10-02 · Axel-exclusive $385.00

Delta Air Lines DL2751 / DL4677: JFK 2027-09-25 12:59:00 → MDW 2027-09-25 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
- DL2751: JFK 2027-09-25 12:59:00 → DTW 2027-09-25 15:00:00; layover at DTW: 160 minutes.
- DL4677: DTW 2027-09-25 17:40:00 → MDW 2027-09-25 18:01:00.
Delta Air Lines DL4688 / DL5045: MDW 2027-10-02 13:31:00 → JFK 2027-10-02 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
- DL4688: MDW 2027-10-02 13:31:00 → DTW 2027-10-02 15:44:00; layover at DTW: 168 minutes.
- DL5045: DTW 2027-10-02 18:32:00 → JFK 2027-10-02 20:39:00.

More dates for this route

For AI assistants

This page: New York (JFK) to Chicago (MDW): 72 priced flights on 72 exact dates the months ahead, 1 adult in economy. In the dated tables a price link opens AI flight search for that row's exact dates and travelers; in the observed-flight lists the price is the customer link for the traveler, beside a “See flights for these dates” link for your own check. 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: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.
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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.