Chicago from West Palm Beach, Oct 23–25: round trip from $489
Chicago is $489 per person round trip from West Palm Beach for Oct 23–25, 2026, a 2-night weekend on an American nonstop. Expect highs of 57–76°F with a small chance of rain, and the best-value hotel, Hilton Chicago, is $522 for the stay.
The flight
$571 $489 per person, round trip
the typical fare on this route
$978 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 | $489 | nonstop | 3h 27m |
| United | $509 | nonstop | 3h 26m |
| American | $489 | nonstop | 3h 29m |
Prices checked Oct 12, 2026, 2:28 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 | $978 |
| Hilton Chicago, 2 nights | $522 |
| Trip total for two | $1,500 |
Regular: $1,664 You pay: $1,500 Saved: $164
the typical fare on this route.
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Why go now
When we checked, the fare was $489 per person round trip, all-in. That's $82 below the typical fare on this route, which is $571, so you'd pay 14% less. It also has the Lowest in 30 days badge: the 12 offers we saw ranged from $489 to $684 per person, and this one is at the bottom of that range. For two, it's $978 on an American nonstop that takes 3h 27m from DJT to ORD. Late October is forecast at 76°F on Friday, 72°F on Saturday and 57°F on Sunday, with a 19% to 33% chance of rain. Pack a light jacket and you're set for walking the Loop, a river cruise and a long afternoon at a museum. Prices change, so take these numbers as what we found today, not a promise.
The kind of trip this is
This is a city weekend built on food, architecture and live music. It's a good fit for a couple or a pair of friends who like to walk and eat well. Two nights moves at a medium pace: a river cruise and a museum during the day, deep-dish and a blues club at night, and a slower Sunday before the flight home. The trip doesn't need a big plan.
Weather in Chicago, Oct 23–25
Highs 57–76°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 76 °F | 67 °F | 33% |
| Sat, Oct 24 | 72 °F | 50 °F | 23% |
| Sun, Oct 25 | 57 °F | 49 °F | 19% |
Where to stay in Chicago
Hilton Chicago is the best value. It's $522 for the 2 nights ($261 a night) for a King Room in The Loop, room only, and it's rated 7.9 from 981 reviews. Hampton Inn Chicago West Loop Fulton Market Area is the top rated at 8.8 from 769 reviews. It costs $683 for the stay ($342 a night), breakfast is included, and it's in the West Loop, where converted warehouses line the restaurant row on Randolph Street. Congress Plaza Hotel Chicago is our budget pick: a 4-star Queen Room at $550 for the stay ($275 a night), rated 7.1 from 4,544 reviews. It's the only one of the three with free cancellation. Staying in The Loop puts architecture, theatres and Millennium Park at your doorstep.
Hilton Chicago
$522 for 2 nights, two guests · $261 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
$683 for 2 nights, two guests · $342 a night
See roomsCongress Plaza Hotel Chicago
$550 for 2 nights, two guests · $275 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 to see the skyline from the water
- See the Bean and the fountains in Millennium Park
- Settle the deep-dish debate at Lou Malnati's or Pequod's
- Spend an afternoon at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
Also worth it
- Eat deep-dish at Lou Malnati's or Pequod's
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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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 | $978 |
| Hotel, 2 nights (Hilton Chicago) | $522 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,020 |
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 | $489 per person |
| Lowest in the last 30 days | $489 (Oct 12, 2026) |
| Typical price, last 60 days | $571 |
| Price checks | 7 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, and the currency is the US dollar.
- Chicago is 1 hour behind West Palm Beach. The flight covers 1,132 miles in 3h 27m.
- The $489 American nonstop leaves DJT at 12:33 PM and lands at ORD at 3:00 PM. Another American nonstop at the same fare leaves at 2:57 PM.
- Prices are all-in, taxes and fees included, as found when we checked. Hilton Chicago and the Hampton Inn don't offer free cancellation.
- Sunday is forecast to cool to a high of 57°F, so bring a layer.
Questions readers ask
How much is the flight?
It's $489 per person round trip, or $978 for two, on an American nonstop. That's all-in, as found when we checked. A United nonstop was $509 per person, leaving at 4:14 PM.
Is this a good price?
Yes. It's $82 below the typical fare on this route, which is $571, so 14% less. It also has the Lowest in 30 days badge. The 12 offers we saw ran from $489 to $684 per person.
Do I need a passport?
No. It's a domestic flight from DJT to Chicago O'Hare (ORD), and you'll pay in US dollars.
What is the weather like?
The forecast is overcast with a high of 76°F on Friday, drizzle with a high of 72°F on Saturday, and overcast with a high of 57°F on Sunday. Rain chances run from 19% to 33%.
Is 2 nights enough?
For a city weekend, yes. You land at 3:00 PM on Friday, which leaves time for dinner. That gives you a full Saturday for the river cruise, Millennium Park and the Art Institute, plus Sunday before you fly home.
What does the whole weekend cost for two?
Our estimate is $2,020 for two: $978 for flights, $522 for 2 nights at Hilton Chicago and $520 for spending, which works out to $130 per person a day.
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Image credits
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License