Chicago (MDW) to New York (JFK), Dec 23, 2026: round trips from $405, one way from $238

Chicago (MDW) to New York (JFK), Dec 23, 2026: round trips from $405, one way from $238 on Axel, checked Nov 13, 2026. Lowest published fares: $405 round trip, Axel-exclusive, Delta Air Lines, 1 stop, Dec 23, 2026 – Jan 4, 2027; $238 one way, Axel-exclusive, Delta Air Lines, 1 stop, Dec 23, 2026; 1 adult, economy, checked Nov 13, 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, labelled with the check date 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 check dates already shown here.

Hotels in New York for these trips

Hotels: under a trip, hotels in New York for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in New York for these nights (Dec 23–24, 2026 · 1 night · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $183 a night · 4★ EVEN Hotel Brooklyn by IHG, $232 a night · 5★ The William Vale, $328 a night
• Hotels in New York for these nights (Dec 23–25, 2026 · 2 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $196 a night, $392 for 2 nights · 4★ EVEN Hotel Brooklyn by IHG, $239 a night, $478 for 2 nights · 5★ The William Vale, $341 a night, $681 for 2 nights
• Hotels in New York for these nights (Dec 23–26, 2026 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $221 a night, $662 for 3 nights · 4★ Penny Williamsburg, $261 a night, $783 for 3 nights · 5★ The William Vale, $373 a night, $1,118 for 3 nights
• Hotels in New York for these nights (Dec 23–27, 2026 · 4 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $236 a night, $942 for 4 nights · 4★ Penny Williamsburg, $265 a night, $1,058 for 4 nights · 5★ The William Vale, $368 a night, $1,472 for 4 nights
• Hotels in New York for these nights (Dec 23–28, 2026 · 5 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $238 a night, $1,189 for 5 nights · 4★ Penny Williamsburg, $269 a night, $1,344 for 5 nights · 5★ The William Vale, $377 a night, $1,885 for 5 nights
• Hotels in New York for these nights (Dec 23–29, 2026 · 6 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $241 a night, $1,443 for 6 nights · 4★ Penny Williamsburg, $273 a night, $1,635 for 6 nights · 5★ The William Vale, $381 a night, $2,288 for 6 nights
• Hotels in New York for these nights (Dec 23–30, 2026 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $251 a night, $1,755 for 7 nights · 4★ Penny Williamsburg, $279 a night, $1,951 for 7 nights · 5★ The William Vale, $385 a night, $2,693 for 7 nights
• Hotels in New York for these nights (Dec 23–31, 2026 · 8 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $263 a night, $2,105 for 8 nights · 4★ EVEN Hotel Brooklyn by IHG, $281 a night, $2,251 for 8 nights · 5★ The William Vale, $390 a night, $3,117 for 8 nights
• Hotels in New York for these nights (Dec 23 – Jan 1, 2027 · 9 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $283 a night, $2,547 for 9 nights · 4★ Penny Williamsburg, $311 a night, $2,795 for 9 nights · 5★ The William Vale, $430 a night, $3,872 for 9 nights
• Hotels in New York for these nights (Dec 23 – Jan 2, 2027 · 10 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $278 a night, $2,777 for 10 nights · 4★ EVEN Hotel Brooklyn by IHG, $310 a night, $3,095 for 10 nights · 5★ The William Vale, $424 a night, $4,238 for 10 nights
• Hotels in New York for these nights (Dec 23 – Jan 3, 2027 · 11 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $270 a night, $2,968 for 11 nights · 4★ EVEN Hotel Brooklyn by IHG, $294 a night, $3,239 for 11 nights · 5★ The William Vale, $419 a night, $4,605 for 11 nights
• Hotels in New York for these nights (Dec 23 – Jan 4, 2027 · 12 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $257 a night, $3,082 for 12 nights · 4★ EVEN Hotel Brooklyn by IHG, $281 a night, $3,370 for 12 nights · 5★ The William Vale, $410 a night, $4,916 for 12 nights
• Hotels in New York for these nights (Dec 23 – Jan 5, 2027 · 13 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $246 a night, $3,194 for 13 nights · 4★ EVEN Hotel Brooklyn by IHG, $269 a night, $3,499 for 13 nights · 5★ The William Vale, $402 a night, $5,224 for 13 nights
• Hotels in New York for these nights (Dec 23 – Jan 6, 2027 · 14 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $236 a night, $3,308 for 14 nights · 4★ EVEN Hotel Brooklyn by IHG, $259 a night, $3,631 for 14 nights · 5★ The William Vale, $395 a night, $5,534 for 14 nights

All hotels in New York

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

2026-12-23 · one way · Axel-exclusive $238

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.

2026-12-23 → 2026-12-24 · Axel-exclusive $450

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2026-12-24 12:59:00 → MDW 2026-12-24 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2026-12-24 12:59:00 → DTW 2026-12-24 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-24 17:40:00 → MDW 2026-12-24 18:01:00.

2026-12-23 → 2026-12-25 · Axel-exclusive $450

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2026-12-25 12:59:00 → MDW 2026-12-25 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2026-12-25 12:59:00 → DTW 2026-12-25 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-25 17:40:00 → MDW 2026-12-25 18:01:00.

2026-12-23 → 2026-12-26 · Axel-exclusive $450

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2026-12-26 12:59:00 → MDW 2026-12-26 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2026-12-26 12:59:00 → DTW 2026-12-26 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-26 17:40:00 → MDW 2026-12-26 18:01:00.

2026-12-23 → 2026-12-27 · Axel-exclusive $450

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2026-12-27 12:59:00 → MDW 2026-12-27 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2026-12-27 12:59:00 → DTW 2026-12-27 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-27 17:40:00 → MDW 2026-12-27 18:01:00.

2026-12-23 → 2026-12-29 · Axel-exclusive $450

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2026-12-29 12:59:00 → MDW 2026-12-29 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2026-12-29 12:59:00 → DTW 2026-12-29 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-29 17:40:00 → MDW 2026-12-29 18:01:00.

2026-12-23 → 2026-12-30 · Axel-exclusive $450

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2026-12-30 12:59:00 → MDW 2026-12-30 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2026-12-30 12:59:00 → DTW 2026-12-30 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-30 17:40:00 → MDW 2026-12-30 18:01:00.

2026-12-23 → 2026-12-31 · Axel-exclusive $450

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• 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.

2026-12-23 → 2027-01-02 · Axel-exclusive $450

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2027-01-02 12:59:00 → MDW 2027-01-02 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-02 12:59:00 → DTW 2027-01-02 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-02 17:40:00 → MDW 2027-01-02 18:01:00.

2026-12-23 → 2027-01-03 · Axel-exclusive $450

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2027-01-03 12:59:00 → MDW 2027-01-03 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-03 12:59:00 → DTW 2027-01-03 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-03 17:40:00 → MDW 2027-01-03 18:01:00.

2026-12-23 → 2027-01-04 · Axel-exclusive $405

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2027-01-04 12:59:00 → MDW 2027-01-04 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-04 12:59:00 → DTW 2027-01-04 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-04 17:40:00 → MDW 2027-01-04 18:01:00.

2026-12-23 → 2027-01-06 · Axel-exclusive $405

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-23 13:31:00 → JFK 2026-12-23 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-23 18:32:00 → JFK 2026-12-23 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2027-01-06 12:59:00 → MDW 2027-01-06 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-06 12:59:00 → DTW 2027-01-06 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-06 17:40:00 → MDW 2027-01-06 18:01:00.

Explore this route

• All dates for this route
• Dec 22, 2026 · Return options
• Dec 24, 2026 · Return options
• Hotels in New York with Axel

For AI assistants

• This page: Chicago (MDW) to New York (JFK) · Dec 23, 2026 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in New York for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total 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 its displayed check date); 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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