Chicago from New York, Oct 16–18: round trip from $363
When we checked, nonstop round trips from New York (JFK) to Chicago (O'Hare) on JetBlue (B6) cost $363 per person, or $725 for two, for Oct 16–18, 2026 (2 nights). The forecast shows highs of 53–61°F with little rain. The best-value hotel is $495 for the stay, or $248 a night.
The flight
$363 per person, round trip
$725 for two, taxes and fees included · JetBlue · nonstop · 5h 14m
Out Fri, Oct 16, 9:30 AM – Fri, Oct 16, 11:24 AM · back Sun, Oct 18, 6:10 AM – Sun, Oct 18, 9:30 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| JetBlue | $363 | nonstop | 5h 14m |
| United | $470 | nonstop | 4h 56m |
| JetBlue | $363 | nonstop | 5h 15m |
Prices checked Oct 11, 2026, 9:02 PM EDT. Prices change; the binding price is the one on the booking site.
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Your trip for two
| For two | |
|---|---|
| Flights for two | $725 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights | $495 |
| Trip total for two | $1,220 |
Tweak this trip
Why go now
We found nonstop round trips at $363 per person, $725 for two, all-in when we checked. That's $1 under the $364 median of our 8 earlier checks on this route. It's a fair price, not a markdown, and those checks have gone as low as $337. The case for going is how the trip is laid out. You leave JFK at 9:30 AM on Friday and land at O'Hare at 11:24 AM local time, so most of Friday is yours in the city. The forecast has highs of 53–61°F, and the chance of rain is 4% on Saturday and 3% on Sunday. That's good walking weather for architecture, museums and long dinners. Mid-October falls between the summer beach season and the holiday markets, so you get the city itself without festival crowds.
The kind of trip this is
This is a city weekend built around food, architecture and nightlife: deep-dish, a river cruise past the skyscrapers, a morning at a museum and blues after dark. It suits a couple or two friends who like to walk and eat well, at a steady but not rushed pace. The flight home leaves early Sunday, so plan on a full Friday and Saturday rather than a lazy three-day stay.
Weather in Chicago, Oct 16–18
Highs 53–61°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 55 °F | 45 °F | 36% |
| Sat, Oct 17 | 53 °F | 42 °F | 4% |
| Sun, Oct 18 | 61 °F | 43 °F | 3% |
Where to stay in Chicago
For location, stay in The Loop, where architecture, theatres and Millennium Park are right outside your door. Hyatt Centric The Loop Chicago is the top-rated pick: 8.5 from 1,005 reviews, $1,059 for the 2 nights ($530 a night), with free cancellation. Cambria Hotel Chicago Loop - Theatre District is the lower-priced Loop option at $855 for the stay ($428 a night). It scores 8.1 from 1,258 reviews and also has free cancellation. Holiday Inn Chicago Midway Airport S by IHG is the best value at $495 for the stay ($248 a night), with 7.5 from 226 reviews. Heads-up: it's by Midway, not O'Hare where the flight lands, and this rate can't be cancelled for free. All three rates are room only, each with a king bed.
Holiday Inn Chicago Midway Airport S by IHG
$495 for 2 nights, two guests · $248 a night
See roomsHyatt Centric The Loop Chicago
$1,059 for 2 nights, two guests · $530 a night
See roomsCambria Hotel Chicago Loop - Theatre District
$855 for 2 nights, two guests · $428 a night
See roomsAll hotels in Chicago for these dates
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Where in Chicago
- The Loop: Architecture, theatres and Millennium Park at your doorstep.
- Magnificent Mile / Streeterville: Shopping on Michigan Avenue and lakefront hotels.
- River North: Galleries, steakhouses and the city's nightlife core.
- West Loop: Converted warehouses with the top restaurant row on Randolph Street.
- Lincoln Park: Leafy neighbourhood with a free zoo and lakefront beaches.
What to do in Chicago
- Take the Chicago Architecture Foundation river cruise for the skyline from the water
- See the Bean and the fountains in Millennium Park, steps from The Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's, and maybe compare both
- Spend a morning at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Friday or Saturday night
Also worth it
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in New York | John F. Kennedy International (JFK), Newark Liberty International (EWR), LaGuardia (LGA) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 5h 14m nonstop |
| Distance | 711 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $726 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | $495 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,741 |
Flights and hotel are the prices we found; spending is a planning estimate for an upscale destination, per person per day times two.
Price history: New York to Chicago
| Per person | |
|---|---|
| This trip | $363 per person |
| Lowest in the last 30 days | $337 (Oct 12, 2026) |
| Typical price, last 60 days | $364 |
| Price checks | 8 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, and you pay in US dollars.
- Chicago is 1 hour behind New York, and the cities are 711 miles apart.
- The return flight leaves at 6:10 AM on Sunday, Oct 18, and lands at 9:30 AM.
- All three hotel rates are room only. The Holiday Inn rate has no free cancellation.
- Prices include taxes and fees as found when we checked, and they can change.
Questions readers ask
How much is the flight?
When we checked, nonstop round trips on JetBlue (B6) were $363 per person, or $725 for two, all-in. That's in line with the $364 median of our 8 earlier checks. Prices change, so the fare you see may be different.
What are the flight times?
On Friday, Oct 16, you leave JFK at 9:30 AM and land at O'Hare at 11:24 AM local time. On Sunday, Oct 18, the return leaves at 6:10 AM and lands at 9:30 AM.
Do I need a passport?
No. It's a domestic trip, you pay in US dollars, and Chicago is 1 hour behind New York.
What's the weather like?
Friday looks overcast, 45–55°F, with a 36% chance of rain. Saturday is partly cloudy, 42–53°F, at 4%. Sunday is clear, 43–61°F, at 3%. Bring a warm layer for the evenings.
Is 2 nights enough?
For a focused city weekend, yes. You land at 11:24 AM on Friday and have all of Saturday, but the 6:10 AM Sunday flight means Sunday is just for getting home.
Can I cancel the hotel?
Hyatt Centric The Loop Chicago ($1,059) and Cambria Hotel Chicago Loop - Theatre District ($855) both come with free cancellation. The Holiday Inn Chicago Midway Airport S by IHG rate ($495) doesn't.
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Image credits
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