New York City from Chicago, Oct 23–25: round trip from $337
A United nonstop from Chicago to New York City costs $337 per person round trip, or $674 for two, for Oct 23–25, 2026 (2 nights). Expect cool days, with highs falling from 63°F to 48°F and some light drizzle. The best-value hotel, Pod Times Square, is $868 for the stay.
The flight
$337 per person, round trip
$674 for two, taxes and fees included · United · nonstop · 2h 29m
Out Fri, Oct 23, 6:00 PM – Fri, Oct 23, 9:29 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| United | $337 | nonstop | 2h 29m |
| Frontier | $350 | 1 stop | 10h 2m |
| United | $337 | nonstop | 2h 23m |
Prices checked Oct 11, 2026, 8:07 PM CDT. 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 | $674 |
| Pod Times Square, 2 nights | $868 |
| Trip total for two | $1,542 |
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Why go now
$337 per person round trip, or $674 for two, gets you a United nonstop that leaves O'Hare at 6:00 PM on Friday and lands at 9:29 PM, so you can go after work. The fare matches the $337 median of our 5 earlier checks on this route. It isn't a markdown, just a fair price for a nonstop. The one-stop Frontier fare we found costs more at $350 and takes 10h 2m. Late October comes before November's NYC Marathon and Macy's Thanksgiving Day Parade. The forecast has highs from 63°F on Friday down to 48°F on Sunday, and no day has a rain chance above 24%. That's jacket weather, and it suits museums, a Broadway show and long walks across the city.
The kind of trip this is
This is a city break built on food, culture and walking: a show, a museum morning, a bridge at sunset and somewhere new for dinner each night. It suits a couple or two friends who like long days on foot and don't mind a compact room. Saturday moves fast and Sunday is slower, and the cooler forecast pushes you indoors toward galleries and theatres.
Weather in New York City, Oct 23–25
Highs 48–63°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 63 °F | 52 °F | 24% |
| Sat, Oct 24 | 53 °F | 46 °F | 21% |
| Sun, Oct 25 | 48 °F | 42 °F | 10% |
Where to stay in New York City
All three hotels are in Manhattan, and all three rates are room only for the 2 nights. Pod Times Square is the best-value pick at $868 for the stay ($434 a night) for a Bunk Pod, with a review score of 8.6 from 16,677 reviews. Park Terrace Hotel is the top-rated pick at 8.9, at $1,648 for the stay ($824 a night) for a Deluxe room. Yotel New York Times Square costs $986 ($493 a night) for a Premium Queen Room with City View and has a review score of 7.4. It's also the only one of the three with free cancellation. Midtown puts you near Times Square and the Broadway theaters, and it has the most hotels to choose from. Heads-up: you can't cancel the Pod or Park Terrace rates for free.
Pod Times Square
$868 for 2 nights, two guests · $434 a night
See roomsPark Terrace Hotel
$1,648 for 2 nights, two guests · $824 a night
See roomsYotel New York Times Square
$986 for 2 nights, two guests · $493 a night
See roomsAll hotels in New York City for these dates
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Where in New York City
- Midtown: Times Square, Broadway theatres and the most hotel choice.
- SoHo / NoLIta: Boutique hotels amid cast-iron streets, shops and restaurants.
- Upper West Side: Quieter residential blocks next to Central Park and museums.
- Williamsburg, Brooklyn: Rooftop bars and skyline views one subway stop from Manhattan.
- Lower Manhattan: Weekend rates near the 9/11 Memorial, ferries and the Brooklyn Bridge.
What to do in New York City
- See a Broadway show on Saturday after a walk through Times Square.
- Walk the High Line to Chelsea Market for lunch.
- Spend Sunday morning at the Met or MoMA while the city is 48°F and drizzly.
- Take the Staten Island Ferry past the Statue of Liberty.
- Cross the Brooklyn Bridge on foot at sunset, or watch it from Top of the Rock instead.
Also worth it
- Spend a morning at the Met or MoMA
- Watch the sunset from Top of the Rock
Tours and tickets in New York City
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Getting there and around
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
|---|---|
| Airports in New York City | John F. Kennedy International (JFK), Newark Liberty International (EWR), LaGuardia (LGA) |
| Flight time | 2h 29m nonstop |
| Distance | 711 miles each way |
| Time difference | +1 hour |
What 2 nights in New York City costs
| Estimate | |
|---|---|
| Flights for two | $674 |
| Hotel, 2 nights (Pod Times Square) | $868 |
| Food, getting around and tickets, 2 days for two | $760 |
| Total for two | $2,302 |
Flights and hotel are the prices we found; spending is a planning estimate for a luxury destination, per person per day times two.
Price history: Chicago to New York City
| Per person | |
|---|---|
| This trip | $337 per person |
| Lowest in the last 30 days | $292 (Oct 12, 2026) |
| Typical price, last 60 days | $337 |
| Price checks | 5 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- You don't need a passport. It's a domestic trip, and you'll pay in US dollars.
- New York is 1 hour ahead of Chicago. The flight covers 711 miles in 2h 29m.
- The fare leaves from O'Hare (ORD). New York has three airports (JFK, Newark EWR and LaGuardia LGA), so check where your fare lands.
- Our budget for two: $674 for flights, $868 for the hotel and $760 for spending, so $2,302 in all, or $190 per person a day.
- Prices include taxes and fees as we found them when we checked, and they can change before you book.
Questions readers ask
How much is the flight?
It's $337 per person round trip, or $674 for two, with taxes and fees included, on a United nonstop. It leaves O'Hare at 6:00 PM on Friday, Oct 23 and lands at 9:29 PM. A later United nonstop costs the same, leaving at 7:55 PM and landing at 11:18 PM.
Is $337 a good price?
It's a fair price. It matches the $337 median of our 5 earlier checks on this route, so it's 0% below that median. The lowest fare we saw in those checks was $292.
Do I need a passport?
No. It's a domestic flight from Chicago, and everything is priced in US dollars. Just bring the ID you normally fly with.
What is the weather like?
Friday: showers, high 63°F and low 52°F, with a 24% chance of rain. Saturday: drizzle, 53°F and 46°F, with a 21% chance. Sunday: drizzle, 48°F and 42°F, with a 10% chance. Pack a warm layer and a light rain jacket.
Is 2 nights enough?
For a quick city weekend, yes. You land Friday night, have all of Saturday for a show and a long walk, and have Sunday for a museum. We didn't find return flight times, so check yours before planning Sunday.
What will the whole weekend cost for two?
Our budget comes to $2,302 for two: $674 for flights, $868 for 2 nights at Pod Times Square and $760 for spending money.
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Image credits
- Photo: Denil Dominic / Pexels, Pexels License
- Photo: Vlad Alexandru Popa / Pexels, Pexels License
- Photo: Pixabay / Pexels, Pexels License