Chicago from New York, 16 – 18 Oct: £1,119 for two, all in
The verdict
Our verdict
Worth it, if
- JetBlue non-stop, 2h 54m, leaving 9:30 AM Friday
- $345 per person, $18 below the typical fare on this route
- Club Quarters in The Loop, rated 8.2 from 5,335 reviews
The catch: Friday has a 75% chance of rain, and a hold bag is about $180 for two, which is not in the total.
Worth it if you want a city weekend of museums, deep-dish and blues; skip it if you need free cancellation at the value hotel.
Worth it if you can live with a wet Friday: $1,484 for two, the flights at $690 plus 2 nights at Club Quarters Hotel Central Loop, Chicago at $794, taxes and fees included. The trip runs Oct 16–18, 2026 (2 nights) on a JetBlue non-stop that takes 2h 54m and leaves at 9:30 AM. A hold bag and spending money aren't in that total.
The total, before you go
£1,119 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £520 |
| Club Quarters Hotel Central Loop, Chicago, 2 nights, two guests, taxes in | £598 |
| The total, before you go | £1,119 |
| Hold luggage each, return (not in the total) | about £136 |
£14 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £34 each way per bag on JetBlue, £136 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
£260 per person, return
£520 for two, taxes and fees included · JetBlue · nonstop · 2h 54m
Out Fri, Oct 16, 9:30 AM – Fri, Oct 16, 11:24 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| JetBlue | £260 | nonstop | 2h 54m |
| American | £262 | nonstop | 2h 49m |
| JetBlue | £260 | nonstop | 2h 55m |
Prices checked 14 Oct 2026, 16:20 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
The fare is $345 per person, $18 below the typical fare on this route, or 5% under it. Across the 12 offers we saw, fares ran from $345 to $365. It's a JetBlue non-stop that takes 2h 54m, so you land at O'Hare at 11:24 AM Friday with most of the day still ahead. Add 2 nights at Club Quarters Hotel Central Loop, Chicago and the trip comes to $1,484 for two with taxes and fees, before bags or spending money. The forecast is mixed but improves: 57°F with a 75% chance of rain on Friday, 58°F with an 18% chance of drizzle on Saturday, and clear skies at 64°F on Sunday. Save the Art Institute for Friday and the river cruise for Sunday. It's a solid autumn city weekend for two at a fair price.
The kind of trip this is
This is a city weekend for two built around architecture, museums, deep-dish and live music. Staying in The Loop puts Millennium Park and the theatres on your doorstep. River North's nightlife and the West Loop's restaurant row on Randolph Street are close by. The pace is easy but full. It suits a couple or a pair of friends who like to walk, eat well and stay out late for a blues set.
Weather in Chicago, 16 – 18 Oct
Highs 57–64°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 57 °F | 49 °F | 75% |
| Sat 17 Oct | 58 °F | 46 °F | 18% |
| Sun 18 Oct | 64 °F | 49 °F | 1% |
Where to stay in Chicago
All three picks are in The Loop, where the architecture, the theatres and Millennium Park are on your doorstep. Club Quarters Hotel Central Loop, Chicago is the best value and the one in our total. It's $794 for the stay ($397 a night) and rated 8.2 from 5,335 reviews, with no free cancellation. Canopy By Hilton Chicago Central Loop is the top-rated pick at 8.9 from 309 reviews and costs $1,044 for the stay ($522 a night). It's the only one of the three with free cancellation. Central Loop Hotel is the budget pick at the same $794 ($397 a night), rated 8.1 from 3,688 reviews, and it also has no free cancellation. For dinner and late nights, River North has the steakhouses and the city's nightlife core.
Club Quarters Hotel Central Loop, Chicago
£598 for 2 nights, two guests · £299 a night
See roomsCanopy By Hilton Chicago Central Loop
£787 for 2 nights, two guests · £393 a night
See roomsCentral Loop Hotel
£598 for 2 nights, two guests · £299 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 on Sunday, the clear day at 64°F
- See the Bean and the fountains in Millennium Park, right in The Loop
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend rainy Friday afternoon at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field if one is on
Also worth it
- Visit the Art Institute of Chicago
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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 | 2h 54m nonstop |
| Distance | 711 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £520 |
| Hotel, 2 nights (Club Quarters Hotel Central Loop, Chicago) | £598 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,511 |
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 | £260 per person |
| Lowest in the last 30 days | £243 (14 Oct 2026) |
| Typical price, last 60 days | £274 |
| Price checks | 23 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- No passport needed, and you pay in US dollars.
- Chicago is 1 hour behind New York; the 711-mile non-stop takes 2h 54m.
- All three hotels are room only, and only the Canopy By Hilton offers free cancellation.
- A hold bag is about $180 for two and is not in the $1,484 total.
- Prices are what we found when we checked, with taxes and fees, and they can change.
Questions readers ask
Is it worth it?
Yes, if a rainy Friday won't bother you. The fare is $345 per person, $18 below the typical fare on this route. The flight is a 2h 54m JetBlue non-stop, and the value hotel in The Loop is rated 8.2. Saturday clears up, and Sunday is clear at 64°F.
How much is the whole trip for two?
It's $1,484 with taxes and fees: $690 for the flights and $794 for 2 nights at Club Quarters Hotel Central Loop, Chicago. A hold bag, about $180 for two, isn't included, and neither is spending money.
What's the weather like?
Friday is 57°F with a 75% chance of rain. Saturday is 58°F with an 18% chance of drizzle, and Sunday is clear at 64°F with a 1% chance of rain. Lows run from 46°F to 49°F, so bring a jacket.
Do I need a passport?
No. It's a domestic trip in US dollars, and Chicago is 1 hour behind New York.
Are 2 nights enough?
For a first look, yes. The flight lands at 11:24 AM Friday, which leaves time for the Art Institute and deep-dish that day. Saturday works for Millennium Park and blues at Kingston Mines, and Sunday morning for the river cruise.
Can I cancel the hotel?
Not at Club Quarters Hotel Central Loop, Chicago or Central Loop Hotel, as neither offers free cancellation. Canopy By Hilton Chicago Central Loop does, at $1,044 for the stay.
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All trips from New York · Chicago from every city · Prices on this route · Trips in October 2026 · Home
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
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