Chicago (MDW) to New York (JFK)

Lowest published fares for the months ahead: $342 round trip, Axel-exclusive, Delta Air Lines, 1 stop, Feb 4–7, 2027; $181 one way, Axel-exclusive, Delta Air Lines, 1 stop, Feb 2, 2027; 73 priced flights on 73 exact dates, 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.

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.

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

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

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

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

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

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

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

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

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

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

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

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

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 (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $207 a night, $621 for 3 nights · 4★ Moxy NYC Downtown, $237 a night, $712 for 3 nights · 5★ The William Vale, $469 a night, $1,406 for 3 nights
• Hotels in New York for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $212 a night, $1,482 for 7 nights · 4★ Moxy NYC Downtown, $268 a night, $1,878 for 7 nights · 5★ The William Vale, $403 a night, $2,823 for 7 nights
• Hotels in New York for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $240 a night, $1,202 for 5 nights · 4★ Moxy NYC Downtown, $295 a night, $1,477 for 5 nights · 5★ The William Vale, $385 a night, $1,923 for 5 nights
• Hotels in New York for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $266 a night, $798 for 3 nights · 4★ Moxy NYC Downtown, $354 a night, $1,061 for 3 nights · 5★ The William Vale, $404 a night, $1,212 for 3 nights
• Hotels in New York for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Pod 39, $243 a night, $729 for 3 nights · 4★ Moxy NYC Downtown, $271 a night, $812 for 3 nights · 5★ The William Vale, $428 a night, $1,283 for 3 nights
• Hotels in New York for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $311 a night, $2,177 for 7 nights · 4★ EVEN Hotel Brooklyn by IHG, $375 a night, $2,627 for 7 nights · 5★ The William Vale, $628 a night, $4,398 for 7 nights
• Hotels in New York for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $442 a night, $1,327 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $534 a night, $1,603 for 3 nights · 5★ The William Vale, $863 a night, $2,588 for 3 nights
• Hotels in New York for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $423 a night, $1,268 for 3 nights · 4★ Moxy NYC Downtown, $457 a night, $1,372 for 3 nights · 5★ The William Vale, $792 a night, $2,376 for 3 nights
• Hotels in New York for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $350 a night, $2,451 for 7 nights · 4★ EVEN Hotel Brooklyn by IHG, $470 a night, $3,290 for 7 nights · 5★ The William Vale, $719 a night, $5,034 for 7 nights
• Hotels in New York for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $369 a night, $1,107 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $526 a night, $1,579 for 3 nights · 5★ The William Vale, $732 a night, $2,196 for 3 nights
• Hotels in New York for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $309 a night, $927 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $454 a night, $1,362 for 3 nights · 5★ The William Vale, $643 a night, $1,929 for 3 nights
• Hotels in New York for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $229 a night, $1,601 for 7 nights · 4★ EVEN Hotel Brooklyn by IHG, $289 a night, $2,022 for 7 nights · 5★ The William Vale, $483 a night, $3,378 for 7 nights
• Hotels in New York for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $244 a night, $731 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $276 a night, $828 for 3 nights · 5★ The William Vale, $486 a night, $1,457 for 3 nights
• Hotels in New York for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $224 a night, $672 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $265 a night, $796 for 3 nights · 5★ The William Vale, $491 a night, $1,472 for 3 nights
• Hotels in New York for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $208 a night, $1,453 for 7 nights · 4★ EVEN Hotel Brooklyn by IHG, $259 a night, $1,814 for 7 nights · 5★ The William Vale, $390 a night, $2,727 for 7 nights
• Hotels in New York for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $225 a night, $1,125 for 5 nights · 4★ Penny Williamsburg, $261 a night, $1,306 for 5 nights · 5★ The William Vale, $365 a night, $1,827 for 5 nights
• Hotels in New York for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $253 a night, $759 for 3 nights · 4★ Penny Williamsburg, $266 a night, $798 for 3 nights · 5★ The William Vale, $381 a night, $1,144 for 3 nights
• Hotels in New York for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $255 a night, $764 for 3 nights · 4★ Penny Williamsburg, $279 a night, $836 for 3 nights · 5★ The William Vale, $401 a night, $1,204 for 3 nights
• Hotels in New York for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $302 a night, $2,115 for 7 nights · 4★ EVEN Hotel Brooklyn by IHG, $323 a night, $2,261 for 7 nights · 5★ The William Vale, $446 a night, $3,120 for 7 nights
• Hotels in New York for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $341 a night, $1,022 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $359 a night, $1,077 for 3 nights · 5★ The William Vale, $515 a night, $1,545 for 3 nights
• Hotels in New York for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $279 a night, $836 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $329 a night, $988 for 3 nights · 5★ The William Vale, $496 a night, $1,488 for 3 nights
• Hotels in New York for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $178 a night, $535 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $179 a night, $538 for 3 nights · 5★ The William Vale, $348 a night, $1,044 for 3 nights
• Hotels in New York for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn, $129 a night, $902 for 7 nights · 4★ Moxy NYC Downtown, $132 a night, $924 for 7 nights · 5★ The William Vale, $328 a night, $2,296 for 7 nights
• Hotels in New York for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $132 a night, $395 for 3 nights · 4★ Moxy NYC Downtown, $119 a night, $358 for 3 nights · 5★ The William Vale, $352 a night, $1,055 for 3 nights
• Hotels in New York for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Feb 26 – Mar 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Feb 27 – Mar 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Mar 26–29, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Mar 27 – Apr 3, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Apr 23–26, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Apr 24 – May 1, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (May 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (May 22–29, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $213 a night, $638 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $246 a night, $739 for 3 nights · 5★ Refinery Hotel New York, $516 a night, $1,548 for 3 nights
• Hotels in New York for these nights (Jun 18–21, 2027 · 3 nights · 2 adults, 1 room): 3★ LIC Hotel, $208 a night, $624 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $232 a night, $697 for 3 nights · 5★ Conrad New York downtown, $476 a night, $1,429 for 3 nights
• Hotels in New York for these nights (Jun 19–26, 2027 · 7 nights · 2 adults, 1 room): 3★ LIC Hotel, $203 a night, $1,423 for 7 nights · 4★ EVEN Hotel Brooklyn by IHG, $235 a night, $1,644 for 7 nights · 5★ Refinery Hotel New York, $599 a night, $4,192 for 7 nights
• Hotels in New York for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $209 a night, $836 for 4 nights · 4★ EVEN Hotel Brooklyn by IHG, $195 a night, $778 for 4 nights · 5★ Refinery Hotel New York, $404 a night, $1,617 for 4 nights
• Hotels in New York for these nights (Jul 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Hampton Inn Brooklyn/Downtown, $235 a night, $705 for 3 nights · 4★ EVEN Hotel Brooklyn by IHG, $212 a night, $636 for 3 nights · 5★ Conrad New York downtown, $476 a night, $1,428 for 3 nights
• Hotels in New York for these nights (Jul 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ La Quinta Inn & Suites by Wyndham Times Square South, $236 a night, $1,654 for 7 nights · 4★ EVEN Hotel Brooklyn by IHG, $191 a night, $1,340 for 7 nights · 5★ Conrad New York downtown, $549 a night, $3,842 for 7 nights
• Hotels in New York for these nights (Aug 13–16, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Aug 14–21, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Sep 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Sep 10–13, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Sep 11–18, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Oct 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel
• Hotels in New York for these nights (Oct 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Pod Brooklyn · 4★ Penny Williamsburg · 5★ The Wall Street Hotel

All hotels in New York

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

2026-11-20 → 2026-11-23 · Axel-exclusive $360

• Delta Air Lines DL4688 / DL5045: MDW 2026-11-20 13:31:00 → JFK 2026-11-20 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-11-20 13:31:00 → DTW 2026-11-20 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-11-20 18:32:00 → JFK 2026-11-20 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2026-11-23 12:59:00 → MDW 2026-11-23 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2026-11-23 12:59:00 → DTW 2026-11-23 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-11-23 17:40:00 → MDW 2026-11-23 18:01:00.

2026-11-24 · one way · Axel-exclusive $247

• Delta Air Lines DL4688 / DL5045: MDW 2026-11-24 13:31:00 → JFK 2026-11-24 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-11-24 13:31:00 → DTW 2026-11-24 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-11-24 18:32:00 → JFK 2026-11-24 20:39:00.

2026-12-03 → 2026-12-06 · Axel-exclusive $360

• Delta Air Lines DL4688 / DL5045: MDW 2026-12-03 13:31:00 → JFK 2026-12-03 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2026-12-03 13:31:00 → DTW 2026-12-03 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2026-12-03 18:32:00 → JFK 2026-12-03 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2026-12-06 12:59:00 → MDW 2026-12-06 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2026-12-06 12:59:00 → DTW 2026-12-06 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-06 17:40:00 → MDW 2026-12-06 18:01:00.

2026-12-17 → 2026-12-20 · Axel-exclusive $405

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

2026-12-26 → 2027-01-02 · Axel-exclusive $450

• 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.
• 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.

2027-01-08 → 2027-01-11 · Axel-exclusive $360

• Delta Air Lines DL4688 / DL5045: MDW 2027-01-08 13:31:00 → JFK 2027-01-08 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-01-08 13:31:00 → DTW 2027-01-08 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-01-08 18:32:00 → JFK 2027-01-08 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2027-01-11 12:59:00 → MDW 2027-01-11 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-11 12:59:00 → DTW 2027-01-11 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-11 17:40:00 → MDW 2027-01-11 18:01:00.

2027-01-22 → 2027-01-25 · Axel-exclusive $360

• 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.
• Delta Air Lines DL2751 / DL4677: JFK 2027-01-25 12:59:00 → MDW 2027-01-25 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-01-25 12:59:00 → DTW 2027-01-25 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-01-25 17:40:00 → MDW 2027-01-25 18:01:00.

2027-02-05 → 2027-02-08 · Axel-exclusive $342

• Delta Air Lines DL4688 / DL5045: MDW 2027-02-05 13:31:00 → JFK 2027-02-05 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-02-05 13:31:00 → DTW 2027-02-05 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-02-05 18:32:00 → JFK 2027-02-05 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2027-02-08 12:59:00 → MDW 2027-02-08 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-02-08 12:59:00 → DTW 2027-02-08 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-02-08 17:40:00 → MDW 2027-02-08 18:01:00.

2027-03-26 → 2027-03-29 · Axel-exclusive $443

• Delta Air Lines DL4688 / DL5045: MDW 2027-03-26 13:31:00 → JFK 2027-03-26 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-03-26 13:31:00 → DTW 2027-03-26 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-03-26 18:32:00 → JFK 2027-03-26 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2027-03-29 12:59:00 → MDW 2027-03-29 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-03-29 12:59:00 → DTW 2027-03-29 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-03-29 17:40:00 → MDW 2027-03-29 18:01:00.

2027-05-28 → 2027-05-31 · Axel-exclusive $472

• Delta Air Lines DL4688 / DL5045: MDW 2027-05-28 13:31:00 → JFK 2027-05-28 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-05-28 13:31:00 → DTW 2027-05-28 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-05-28 18:32:00 → JFK 2027-05-28 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2027-05-31 12:59:00 → MDW 2027-05-31 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-05-31 12:59:00 → DTW 2027-05-31 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-05-31 17:40:00 → MDW 2027-05-31 18:01:00.

2027-08-13 → 2027-08-16 · Axel-exclusive $410

• Delta Air Lines DL4688 / DL5045: MDW 2027-08-13 13:31:00 → JFK 2027-08-13 20:39:00; 1 stop(s) via DTW; 368 minutes. Local airport times.
  • DL4688: MDW 2027-08-13 13:31:00 → DTW 2027-08-13 15:44:00; layover at DTW: 168 minutes.
  • DL5045: DTW 2027-08-13 18:32:00 → JFK 2027-08-13 20:39:00.
• Delta Air Lines DL2751 / DL4677: JFK 2027-08-16 12:59:00 → MDW 2027-08-16 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-08-16 12:59:00 → DTW 2027-08-16 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-08-16 17:40:00 → MDW 2027-08-16 18:01:00.

2027-10-02 → 2027-10-09 · Axel-exclusive $410

• 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.
• Delta Air Lines DL2751 / DL4677: JFK 2027-10-09 12:59:00 → MDW 2027-10-09 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL2751: JFK 2027-10-09 12:59:00 → DTW 2027-10-09 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2027-10-09 17:40:00 → MDW 2027-10-09 18:01:00.

More dates for this route

• Nov 20, 2026 · Return options
• Nov 28, 2026 · Return options
• Dec 11, 2026 · Return options
• Dec 22, 2026 · Return options
• Dec 31, 2026 · Return options
• Jan 9, 2027 · Return options
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• Hotels in New York with Axel

For AI assistants

• This page: Chicago (MDW) to New York (JFK): 73 priced flights on 73 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 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: 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.
• 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 Chicago to New York (JFK) 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.

Feedback (optional): Missing info · Axel issue