New York City from Chicago, 23 – 25 Oct: £1,162 for two, all in
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The verdict
Our verdict
Worth it, if
- 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
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.
Worth it if you don't mind sleeping in a bunk pod: $1,542 for two, which is the United flights at $674 plus Pod Times Square at $868, taxes and fees included. Checked bags and spending money aren't in that total. You leave Friday, Oct 23 and come home Sunday, Oct 25 (2 nights), flying nonstop from O'Hare in 2h 29m.
The total, before you go
£1,162 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £508 |
| Pod Times Square, 2 nights, two guests, taxes in | £654 |
| The total, before you go | £1,162 |
| Hold luggage each, return (not in the total) | about £121 |
Not in it: seat selection on basic fares and hold luggage (about £30 each way per bag on United, £121 for two return); a resort fee, if the hotel has one, is collected at the desk. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
£254 per person, return
£508 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 | £254 | nonstop | 2h 29m |
| Frontier | £264 | 1 stop | 10h 2m |
| United | £254 | nonstop | 2h 23m |
Prices checked 11 Oct 2026, 20:07 GMT-5. Prices change; the binding price is the one on the booking site.
Paid links: when you book through a link on this page, the booking site pays us a referral fee. Your price does not change. How we earn
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Why now
At $337 per person, the United nonstop sits right at the median of our earlier checks on this route, so you're paying the going rate, not a premium. With Pod Times Square, the whole trip comes to $1,542 for two. That doesn't cover a checked bag (about $160 for two) or spending money. Late October means jacket weather: highs of 63°F Friday, 53°F Saturday and 48°F Sunday, with rain chances of 24%, 21% and 10%. That's good walking weather for the High Line or the Brooklyn Bridge, and if the drizzle shows up, the Met or MoMA can fill a morning. The 6:00 PM departure lets you leave after work on Friday and still land by 9:29 PM, so you get all of Saturday in the city.
The kind of trip this is
This is a quick city weekend for two: a show, a museum morning, long walks and late dinners. It suits a couple or two friends who like to keep moving and won't spend much time in the room. The pace is full but compact: you arrive Friday night, have a big Saturday and get a Sunday morning out before heading home.
Weather in New York City, 23 – 25 Oct
Highs 48–63°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 63 °F | 52 °F | 24% |
| Sat 24 Oct | 53 °F | 46 °F | 21% |
| Sun 25 Oct | 48 °F | 42 °F | 10% |
Where to stay in New York City
Pod Times Square is the best-value pick at $868 for the stay ($434 a night). It scores 8.6 from 16,677 reviews, but the room is a Bunk Pod and there's no free cancellation. Park Terrace Hotel is the top-rated pick at 8.9 from 2,216 reviews and costs $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 scores 7.4 from 7,608 reviews. It's the only one of the three with free cancellation, which makes it the flexible pick. Both Times Square hotels put you in Midtown, close to Broadway theatres and the most hotel choice in the city.
Pod Times Square
£654 for 2 nights, two guests · £327 a night
See roomsPark Terrace Hotel
£1,242 for 2 nights, two guests · £621 a night
See roomsYotel New York Times Square
£743 for 2 nights, two guests · £372 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 after a walk through Times Square
- Walk the High Line to Chelsea Market
- Take the Staten Island Ferry past the Statue of Liberty
- Spend a morning at the Met or MoMA
- Cross the Brooklyn Bridge on foot at sunset
- 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 | £508 |
| Hotel, 2 nights (Pod Times Square) | £654 |
| Food, getting around and tickets, 2 days for two | £573 |
| Total for two | £1,735 |
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 | £254 per person |
| Lowest in the last 30 days | £220 (12 Oct 2026) |
| Typical price, last 60 days | £254 |
| Price checks | 5 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for New York City.
- Currency: US dollar (USD).
- No passport needed, and you pay in US dollars.
- New York is 1 hour ahead of Chicago, and the 711-mile flight takes 2h 29m.
- A later United nonstop leaves at 7:55 PM and lands at 11:18 PM, also $337 per person.
- Resort fees, checked bags (about $160 for two) and spending money are not in the $1,542 total.
- Prices are all-in as we found them when we checked, and they can change.
Questions readers ask
Is it worth it?
Yes, if bunks are fine for you. The fare is $337 per person on a 2h 29m United nonstop, right at the median of our earlier checks. Pod Times Square scores 8.6, but it has no free cancellation.
How much is the whole trip for two?
$1,542 all in: $674 for the flights plus $868 for 2 nights at Pod Times Square. A checked bag adds about $160 for two. Our budget also sets aside $760 for spending money, which brings it to $2,302.
What is the weather like?
Cool and mostly dry. Highs are 63°F Friday, 53°F Saturday and 48°F Sunday, with lows of 52°F, 46°F and 42°F. Rain chances are 24%, 21% and 10%, so pack a light rain jacket.
Is 2 nights enough?
For a first taste, yes. You land at 9:29 PM Friday, then have all of Saturday and Sunday morning for a show, a museum and a walk across the Brooklyn Bridge.
What if we want a real bed or a way to cancel?
Yotel New York Times Square has a Premium Queen Room with City View for $986 for the stay, with free cancellation. Park Terrace Hotel is $1,648 for a Deluxe room and scores 8.9.
Do I need a passport?
No. It's a domestic trip, so you just need the ID you'd normally fly with, and you pay in US dollars.
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: Denil Dominic / Pexels, Pexels License
- Photo: Vlad Alexandru Popa / Pexels, Pexels License
- Photo: Pixabay / Pexels, Pexels License