Chicago from Fort Lauderdale, Oct 23–25: round trip from $225
Chicago from Fort Lauderdale is $225 per person round trip ($449 for two) for Oct 23–25, 2026, 2 nights, on Frontier (F9) with 1 stop rather than nonstop. Forecast highs are 59–68°F with a small chance of showers. Our best-value hotel, Hilton Chicago in The Loop, is $522 for the stay, or $261 a night.
The flight
$397 $225 per person, round trip
the highest fare we saw for these dates
$449 for two, taxes and fees included · Frontier · 1 stop · 17h 42m
Out Fri, Oct 23, 9:58 PM – Sat, Oct 24, 11:32 AM · back Sun, Oct 25, 8:04 AM – Sun, Oct 25, 12:12 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $225 | 1 stop | 17h 42m |
| Frontier | $248 | nonstop | 3h 23m |
| JetBlue | $282 | nonstop | 6h 23m |
Prices checked Oct 12, 2026, 6:02 AM 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 | $449 |
| Hilton Chicago, 2 nights | $522 |
| Trip total for two | $971 |
Regular: $1,316 You pay: $971 Saved: $345
the highest fare we saw for these dates.
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Why go now
At $225 per person round trip, this fare is $172 below the highest fare we saw for these dates, which was $397. That's 43% under it, out of 12 fares we checked for this weekend. Prices are all-in, taxes and fees included, as found when we checked, and they can change. Add the Hilton Chicago at $522 for two nights and $520 for spending, and the whole weekend comes to $1,492 for two. Late October falls between summer beach season and the holiday markets, so this trip is about museums, food and architecture, not lakefront swims. The forecast shows highs of 59–68°F and a 26–33% chance of showers each day. That's jacket weather, and it works fine for a river cruise, an afternoon at the Art Institute and a deep-dish dinner.
The kind of trip this is
A city weekend built around food, culture and nightlife: architecture from the river, the Art Institute, deep-dish and a blues club after dark. It suits a couple or two friends who like walking and don't mind full days. The pace is quick, because the cheapest flight lands Saturday at 11:32 AM and the return leaves Sunday at 8:04 AM.
Weather in Chicago, Oct 23–25
Highs 59–68°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 68 °F | 56 °F | 33% |
| Sat, Oct 24 | 59 °F | 52 °F | 32% |
| Sun, Oct 25 | 64 °F | 54 °F | 26% |
Where to stay in Chicago
Hilton Chicago is the best value at $522 for the 2 nights ($261 a night). That gets you a King Room, rated 7.9 from 981 reviews, in The Loop, with the architecture, theatres and Millennium Park right outside. It's room only, with no free cancellation. SpringHill Suites by Marriott Chicago Chinatown is the top rated at 8.9 from 639 reviews: $586 for the stay ($293 a night) for a King Suite with Sofa Bed, breakfast included. It's also non-refundable. The Tremont Chicago Hotel is the budget pick at $400 ($200 a night) and the only one with free cancellation. Heads-up: its 5.7 score comes from just 8 reviews. For dinners out, the West Loop has the restaurant row on Randolph Street, and River North is the center of the city's nightlife.
Hilton Chicago
$522 for 2 nights, two guests · $261 a night
See roomsSpringHill Suites by Marriott Chicago Chinatown
$586 for 2 nights, two guests · $293 a night
See roomsThe Tremont Chicago Hotel
$400 for 2 nights, two guests · $200 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, right in The Loop.
- Eat deep-dish at Lou Malnati's or Pequod's and pick a side.
- Spend a rainy afternoon at the Art Institute of Chicago.
- Hear live blues at Kingston Mines on Saturday night.
- Walk Lincoln Park for the free zoo and the lakefront.
Also worth it
- Visit the Art Institute of Chicago
- Catch a Cubs game at Wrigley Field
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Getting there and around
| Airports in Fort Lauderdale | Fort Lauderdale-Hollywood International (FLL) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 17h 42m (1 stop) |
| Distance | 1,169 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $450 |
| Hotel, 2 nights (Hilton Chicago) | $522 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,492 |
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: Fort Lauderdale to Chicago
| Per person | |
|---|---|
| This trip | $225 per person |
| Lowest in the last 30 days | $223 (Oct 12, 2026) |
| Price checks | 3 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed: it's a domestic trip, and you pay in US dollars.
- Chicago is 1 hour behind Fort Lauderdale, and the route covers 1,169 miles.
- The $225 fare is Frontier (F9) with 1 stop: it leaves 9:58 PM Friday and lands 11:32 AM Saturday, 17h 42m in all.
- Of the three hotels, only The Tremont Chicago Hotel has free cancellation; the other two are non-refundable as found.
- Prices include taxes and fees as found when we checked; they can change before you book.
Questions readers ask
How much is the flight?
$225 per person round trip, $449 for two, on Frontier (F9) with 1 stop. You head home Sunday, Oct 25, leaving at 8:04 AM and landing at 12:12 PM.
Is there a nonstop option?
Yes. We found a Frontier nonstop at $248 per person. It leaves Friday at 1:07 PM and lands at 3:30 PM, a 3h 23m flight. We also found a B6 nonstop at $282 per person, leaving at 9:15 PM Friday.
Is 2 nights enough?
It's tight on the $225 fare. You land Saturday at 11:32 AM and fly out Sunday at 8:04 AM, so you get about one full day. The $248 nonstop lands Friday at 3:30 PM and gives you an extra evening.
What is the weather like?
Friday has a high of 68°F with showers, Saturday is overcast at 59°F, and Sunday reaches 64°F with showers. Lows run 52–56°F and the chance of rain is 26–33% each day, so pack a light jacket.
Do I need a passport?
No. It's a domestic trip, so you just need your usual ID, and everything is priced in US dollars.
What does the whole weekend cost?
We estimate $1,492 for two: $450 for flights, $522 for the Hilton Chicago and $520 for spending, which is $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