Chicago from West Palm Beach, 23 – 25 Oct: £1,131 for two, all in
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The verdict
Our verdict
Worth it, because
- 3h 27m American nonstop, leaving 12:33 PM Friday, Oct 23
- $489 per person, $82 below the typical fare on this route
- Hilton Chicago in The Loop, 7.9 from 981 reviews
The catch: A checked bag is about $160 for two and isn't in the total, and Hilton Chicago doesn't offer free cancellation.
Worth it if you want museums, deep-dish and live music over two days; skip it if you need a beach or a slow pace.
Worth it, because a nonstop city weekend for the two of you comes in under the usual fare. The whole trip is $1,500 for two: flights at $978 plus 2 nights at Hilton Chicago at $522, taxes and fees included, with checked bags and spending money not in that total. You fly Friday, Oct 23 and come home Sunday, Oct 25, 2026, nonstop on American.
The total, before you go
£1,131 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £737 |
| Hilton Chicago, 2 nights, two guests, taxes in | £393 |
| The total, before you go | £1,131 |
| Hold luggage each, return (not in the total) | about £121 |
£62 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £30 each way per bag on American, £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
£369 per person, return
£737 for two, taxes and fees included · American · nonstop · 3h 27m
Out Fri, Oct 23, 12:33 PM – Fri, Oct 23, 3:00 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| American | £369 | nonstop | 3h 27m |
| United | £384 | nonstop | 3h 26m |
| American | £369 | nonstop | 3h 29m |
Prices checked 12 Oct 2026, 14:28 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
At $489 per person, this nonstop is $82 below the typical fare on this route, 14% under the $571 we usually see, and it carries the Lowest in 30 days badge. Across 12 offers we checked, fares ran from $489 to $684, so you're looking at the bottom of the range. The weather works for walking the city: Friday tops out at 76°F, Saturday at 72°F with a 23% chance of drizzle, and Sunday cools to 57°F. That's jacket-in-the-bag weather, not a washout. The 12:33 PM departure lands you at O'Hare at 3:00 PM Chicago time, early enough for a river cruise or dinner in the West Loop the first evening. Prices are what we found when we checked, all-in, and they can change.
The kind of trip this is
A city weekend built around food, architecture and music. It suits a couple or two friends who like to walk all day, eat well and stay out for a set of blues. The pace is full but easy: two nights, one flight each way, and most of the big sights clustered around The Loop and the river, so you spend your time in the city, not getting across it.
Weather in Chicago, 23 – 25 Oct
Highs 57–76°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 76 °F | 67 °F | 33% |
| Sat 24 Oct | 72 °F | 50 °F | 23% |
| Sun 25 Oct | 57 °F | 49 °F | 19% |
Where to stay in Chicago
Hilton Chicago is the best-value pick and the one in the total: $522 for the stay, or $261 a night, a King Room with a 7.9 score from 981 reviews, room only, no free cancellation. It sits in The Loop, with architecture, theatres and Millennium Park at your doorstep. Hampton Inn Chicago West Loop Fulton Market Area is the top-rated option at 8.8 from 769 reviews, $683 for the stay or $342 a night, with breakfast included, and it puts you in the West Loop near the restaurant row on Randolph Street. Congress Plaza Hotel Chicago is $550 for the stay or $275 a night, scored 7.1 from 4,544 reviews, also in The Loop, and it's the only one of the three with free cancellation.
Hilton Chicago
£393 for 2 nights, two guests · £197 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
£515 for 2 nights, two guests · £258 a night
See roomsCongress Plaza Hotel Chicago
£415 for 2 nights, two guests · £207 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, a short walk from The Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend a morning at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field
Also worth it
- Visit the Art Institute of Chicago
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Getting there and around
| Airports in West Palm Beach | President Donald J. Trump International (Palm Beach) (DJT) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 3h 27m nonstop |
| Distance | 1,132 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £737 |
| Hotel, 2 nights (Hilton Chicago) | £393 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,523 |
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: West Palm Beach to Chicago
| Per person | |
|---|---|
| This trip | £369 per person |
| Lowest in the last 30 days | £369 (12 Oct 2026) |
| Typical price, last 60 days | £430 |
| Price checks | 7 |
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 West Palm Beach; the nonstop covers 1,132 miles in 3h 27m.
- The flight leaves Palm Beach (DJT) at 12:33 PM and lands at Chicago O'Hare (ORD) at 3:00 PM.
- A checked bag is about $160 for two on top of the $1,500 total.
- We estimate about $130 per person per day for food and spending, $520 for two.
Questions readers ask
Is it worth it?
Yes for a couple or two friends after a city weekend. The fare is 14% under the typical fare, the flight is nonstop, and the forecast highs run 57–76°F.
How much is the whole trip for two?
$1,500, all in: $978 for two round-trip fares on American plus $522 for 2 nights at Hilton Chicago. Checked bags, about $160 for two, and spending money are extra.
What's the weather like?
Friday is overcast with a high of 76°F, Saturday 72°F with a 23% chance of drizzle, and Sunday overcast at 57°F with lows near 49°F. Pack a layer.
Is 2 nights enough?
For a first look, yes. With a 3:00 PM arrival on Friday you can fit a river cruise, Millennium Park, the Art Institute and a night of blues before Sunday.
Do I need a passport?
No. It's a domestic flight from Palm Beach to Chicago O'Hare, and everything is in US dollars.
Can I cancel the hotel?
Hilton Chicago and the Hampton Inn listed here don't offer free cancellation. Congress Plaza Hotel Chicago does, at $550 for the stay.
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All trips from West Palm Beach · 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
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License