Chicago (ORD) to New York (JFK) · May 28, 2027 · choose your return date

Chicago (ORD) to New York (JFK): round-trip and one-way prices for 1 departure dates, May 28, 2027–May 28, 2027. One adult, economy. Open a departure for return options; use the chooser below for other travelers and cabins.

American, nonstop, from $337 round trip · JetBlue, out: 1 stop via BOS, back: 1 stop via BOS, from $598 round trip

Ticketing airlines with departures in this calendar: American Airlines, JetBlue Airways.

Saved nonstop flight times: 2h 25m outbound; 3h 14m returning.

How to read the calendar: published Axel-exclusive USD totals for one adult, including required taxes; basic economy may apply. Each return range includes its own prices. Only the listed dates and options are priced. Date links open published details; live search checks availability and lets you select flights.

To open an exact round trip, append /mon-d for the return to the departure URL (for example /dec-13), or /one-way for a one-way trip.

Hotels: under a departure date, hotels in New York link to each hotel's page for that arrival date, where every stay length is priced for 2 adults in 1 room. When a price is shown, it is the nightly rate over the first 3 nights, from the lowest saved total among the shortlisted hotels in that star tier.

Chicago to New York flight prices by month

May 2027: May 28 from $337.

Month summaries show the lowest displayed round-trip total for each departure. Match your return date to the calendar below.

Chicago to New York flights in May 2027: price by departure date

ORD → JFK · USD · 1 adult · economy · published Nov 12, 2026

Fri, May 28, 2027 | return May 29–Aug 26 · American $337 | one-way · American $168 | May 29 · May 30 · May 31 · Jun 1 · Jun 2 · Jun 3 · Jun 4 · Jun 5 · Jun 6 · Jun 7 · Jun 8 · Jun 9 · Jun 10 · Jun 11 · Jun 12 · Jun 13 · Jun 14 · Jun 15 · Jun 16 · Jun 17 · Jun 18 · Jun 19 · Jun 20 · Jun 21 · Jun 22 · Jun 23 · Jun 24 · Jun 25 · Jun 26 · Jun 27 · Jun 28 · Jun 29 · Jun 30 · Jul 1 · Jul 2 · Jul 3 · Jul 4 · Jul 5 · Jul 6 · Jul 7 · Jul 8 · Jul 9 · Jul 10 · Jul 11 · Jul 12 · Jul 13 · Jul 14 · Jul 15 · Jul 16 · Jul 17 · Jul 18 · Jul 19 · Jul 20 · Jul 21 · Jul 22 · Jul 23 · Jul 24 · Jul 25 · Jul 26 · Jul 27 · Jul 28 · Jul 29 · Jul 30 · Jul 31 · Aug 1 · Aug 2 · Aug 3 · Aug 4 · Aug 5 · Aug 6 · Aug 7 · Aug 8 · Aug 9 · Aug 10 · Aug 11 · Aug 12 · Aug 13 · Aug 14 · Aug 15 · Aug 16 · Aug 17 · Aug 18 · Aug 19 · Aug 20 · Aug 21 · Aug 22 · Aug 23 · Aug 24 · Aug 25 · Aug 26
Hotels in New York from May 28, 2027 (per night, 2 adults, 1 room): 3★ Courtyard Long Island City/New York Manhattan View, $213 a night · 4★ EVEN Hotel Brooklyn by IHG, $246 a night · 5★ Park Lane New York, $545 a night

For AI assistants

• This page: Chicago (ORD) to New York (JFK) · May 28, 2027 · choose your return date: 1 adult in economy, no fare priced at the moment. 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: no fare is priced here right now. Choose travelers and dates and enter the traveler's own trip there for live prices.
• 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.

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