Chicago from Fort Lauderdale, Oct 16–18: round trip from $297
Chicago from Fort Lauderdale is $297 per person round trip ($594 for two) for Oct 16–18, 2026, 2 nights, nonstop on Frontier. The forecast shows highs of 53–62°F, with drizzle on Friday and clear skies Saturday and Sunday. The best-value hotel, Holiday Inn Chicago Midway Airport S by IHG, is $490 for the stay.
The flight
$297 per person, round trip
$594 for two, taxes and fees included · Frontier · nonstop · 3h 23m
Out Fri, Oct 16, 1:07 PM – Fri, Oct 16, 3:30 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $297 | nonstop | 3h 23m |
| Frontier | $358 | 1 stop | 16h 6m |
| Frontier | $361 | 1 stop | 14h 53m |
Prices checked Oct 12, 2026, 2:23 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 | $594 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights | $490 |
| Trip total for two | $1,084 |
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Why go now
Here's the honest number first: $297 per person round trip, $594 for two, is $24 above $273, the median of 6 earlier checks on this route, and the low in the last 30 days was $223. So this isn't a price drop. It's a nonstop on Frontier, 3h 23m, leaving Friday at 1:07 PM and landing at 3:30 PM, with time left for dinner. Add the $490 hotel and our $520 spending estimate, and the weekend for two comes to $1,604. Mid-October means cool city weather: 57°F with drizzle on Friday, then clear at 53°F on Saturday and 62°F on Sunday. That's good walking weather for architecture, museums and deep-dish, and Sunday looks like the nicest day for the lakefront.
The kind of trip this is
This is a city long weekend built around food, culture and architecture. It suits a couple or two friends who like to walk, eat well and hear live music at night. The pace is quick: you get a Friday evening, one full Saturday and a Sunday before the flight home, so pick a neighborhood and do it properly rather than chasing every sight.
Weather in Chicago, Oct 16–18
Highs 53–62°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 57 °F | 46 °F | 51% |
| Sat, Oct 17 | 53 °F | 45 °F | 2% |
| Sun, Oct 18 | 62 °F | 46 °F | 2% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best value at $490 for the 2 nights ($245 a night). It's 3 stars and rated 7.5 from 224 reviews, and it sits by Midway Airport rather than in a central area. Canopy By Hilton Chicago Central Loop is the top rated, at 8.9 from 308 reviews. It's 4 stars and $962 for the stay ($481 a night), and it's in The Loop, with architecture, theatres and Millennium Park at your doorstep. Hotel Chicago West Loop, SureStay Collection by Best Western costs $685 ($343 a night). It's 2 stars, rated 7.4 from 877 reviews, and it's the only one of the three with free cancellation. The West Loop puts you close to the restaurant row on Randolph Street. All three are room only.
Holiday Inn Chicago Midway Airport S by IHG
$490 for 2 nights, two guests · $245 a night
See roomsCanopy By Hilton Chicago Central Loop
$962 for 2 nights, two guests · $481 a night
See roomsHotel Chicago West Loop, SureStay Collection by Best Western
$685 for 2 nights, two guests · $343 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 clear Saturday or Sunday.
- See the Bean and the fountains in Millennium Park.
- Eat deep-dish at Lou Malnati's or Pequod's.
- Spend drizzly Friday afternoon at the Art Institute of Chicago.
- Hear live blues at Kingston Mines on Saturday night.
- Walk the leafy streets of Lincoln Park, with its free zoo and lakefront beaches.
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 | 3h 23m nonstop |
| Distance | 1,169 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $594 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | $490 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,604 |
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 | $297 per person |
| Lowest in the last 30 days | $223 (Oct 12, 2026) |
| Typical price, last 60 days | $273 |
| Price checks | 6 |
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. The nonstop covers 1,169 miles in 3h 23m, FLL to O'Hare (ORD).
- Prices are all-in, taxes and fees included, as found when we checked. They can change before you book.
- All three hotels are room only. Only Hotel Chicago West Loop, SureStay Collection by Best Western offers free cancellation.
Questions readers ask
How much is the flight?
$297 per person round trip, $594 for two, nonstop on Frontier. The outbound leaves Fort Lauderdale on Friday, Oct 16 at 1:07 PM and lands at O'Hare at 3:30 PM. The price includes taxes and fees as found and can change.
Do I need a passport?
No. Chicago is a domestic trip from Fort Lauderdale, and the currency is the US dollar.
What is the weather like?
Cool. Friday shows a high of 57°F with a 51% chance of drizzle. Saturday is clear at 53°F and Sunday is clear at 62°F, with lows around 45°F to 46°F, so pack a jacket.
Is 2 nights enough?
For a focused city weekend, yes. You land at 3:30 PM Friday, so you get a full Saturday and most of Sunday. Pick a river cruise, a museum, deep-dish and a blues night rather than trying to cover everything.
What does the whole weekend cost for two?
Our estimate is $1,604: $594 for flights, $490 for the best-value hotel and $520 for spending, which works out to $130 per person per day.
Is $297 a good price for this route?
It's $24 above $273, the median of our 6 earlier checks, and we saw $223 in the last 30 days. What you get is a nonstop on a weekend with a clear forecast.
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Image credits
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