Chicago to New York City: what the flight costs
In the last 60 days we checked this route 19 times. The typical return was £262 per person and the lowest £184, taxes and fees included.
| Per person | |
|---|---|
| Lowest seen | £184 |
| Typical (median) | £262 |
| Price checks, 60 days | 19 |
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Trips we picked on this route
A week away · from ChicagoLowest in 30 daysWorth it, if
New York City
14 – 21 Nov 2026 · 7 nights
- $244 per person, $104 below the typical fare on this route
- Pod 51 scores 8.2 from 9,513 reviews, with free cancellation
- Met or MoMA mornings, highs of 45–55°F for walking the High Line
£1,574 for two · 7 nights · flights, hotel, taxes & fees
Flights £368 + hotel £1,206, taxes in · a checked bag each adds about £181
Frontier · with a stop · 9h 30m
The catch: The Frontier fare has one stop and takes 9h 30m, and Pod 51's room is a bunk pod with a shared bathroom.
Worth it if a long travel day and a bunk pod are fine for a week in New York; skip it if you need a private bathroom.
The weekend after · from ChicagoWorth it, if
New York City
23 – 25 Oct 2026 · 2 nights
- United nonstop from O'Hare, 2h 29m, landing 9:29 PM Friday
- $337 per person, matching the median of our earlier checks
- Pod Times Square scores 8.6 from 16,677 reviews, in Times Square
£1,162 for two · 2 nights · flights, hotel, taxes & fees
Flights £508 + hotel £654, taxes in · a checked bag each adds about £121
United · nonstop · 2h 29m
The catch: The best-value room is a Bunk Pod with no free cancellation, and a checked bag is about $160 for two, which isn't in the total.
Worth it if you want Broadway and museums on a packed weekend and don't mind bunks; skip it if you want room to spread out.
Every fare we found in the last 30 days
| Checked | Trip dates | Per person | Airline | Stops | Duration | Source |
|---|---|---|---|---|---|---|
| 14 Oct 2026 | 14 – 21 Nov 2026 | £184 | Frontier | with a stop | 9h 30m | Google Flights |
| 14 Oct 2026 | 14 – 21 Nov 2026 | £238 | B6 | with a stop | 5h 59m | Kiwi.com |
| 14 Oct 2026 | 23 – 25 Oct 2026 | £366 | B6 | with a stop | 2h 20m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £340 | B6 | nonstop | 2h 22m | Kiwi.com |
| 14 Oct 2026 | 14 – 21 Nov 2026 | £184 | Frontier | with a stop | 9h 30m | Google Flights |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £262 | Frontier | with a stop | 27h 52m | Google Flights |
| 14 Oct 2026 | 14 – 21 Nov 2026 | £238 | B6 | with a stop | 5h 59m | Kiwi.com |
| 14 Oct 2026 | 23 – 25 Oct 2026 | £366 | B6 | with a stop | 2h 20m | Kiwi.com |
| 14 Oct 2026 | 16 – 18 Oct 2026 | £340 | B6 | nonstop | 2h 22m | Kiwi.com |
| 13 Oct 2026 | 14 – 21 Nov 2026 | £238 | B6 | with a stop | 5h 59m | Kiwi.com |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £340 | B6 | nonstop | 2h 22m | Kiwi.com |
| 13 Oct 2026 | 14 – 21 Nov 2026 | £238 | B6 | with a stop | 5h 59m | Kiwi.com |
| 13 Oct 2026 | 23 – 25 Oct 2026 | £370 | B6 | with a stop | 2h 22m | Kiwi.com |
| 13 Oct 2026 | 16 – 18 Oct 2026 | £352 | B6 | nonstop | 2h 22m | Kiwi.com |
| 11 Oct 2026 | 23 – 25 Oct 2026 | £254 | United | nonstop | 2h 29m | Google Flights |
| 11 Oct 2026 | 16 – 18 Oct 2026 | £220 | Frontier | with a stop | 27h 52m | Google Flights |
| 11 Oct 2026 | 14 – 21 Nov 2026 | £240 | B6 | with a stop | 5h 59m | Kiwi.com |
| 11 Oct 2026 | 23 – 25 Oct 2026 | £353 | B6 | with a stop | 2h 22m | Kiwi.com |
| 11 Oct 2026 | 16 – 18 Oct 2026 | £378 | B6 | nonstop | 2h 22m | Kiwi.com |
About New York City
New York City delivers Broadway, world-class museums, skyline views and a restaurant for every cuisine on earth, all reachable by subway.
New York City from every city: when to go, where to stay, what to do
Questions about Chicago to New York City
What does a return from Chicago to New York City usually cost?
Over the last 60 days the typical price we found was £262 per person, taxes and fees included, across 19 checks; the lowest was £184.
When is the best time to fly from Chicago to New York City?
New York City is at its best in April, May, June, September, October, November and December. Avoid January, February: Cold, grey and slushy, though hotel rates are at their lowest
Do I need a passport to fly from Chicago to New York City?
No passport needed for travellers from the United States: a government photo ID is enough for New York City.
Prices converted from US dollars at the rate of 15 Oct 2026.