Chicago from Fort Myers, Oct 16–18: round trip from $494
Round-trip flights from Fort Myers to Chicago are $494 per person ($988 for two) for Oct 16–18, 2026, which is 2 nights, on Frontier with one stop. Highs run 52–62°F, and rain is likely only on Friday. The best-value hotel is $501 for the stay.
The flight
$592 $494 per person, round trip
the typical fare on this route
$988 for two, taxes and fees included · Frontier · 1 stop · 10h 54m
Out Fri, Oct 16, 12:45 PM – Fri, Oct 16, 10:39 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $494 | 1 stop | 10h 54m |
| American | $545 | nonstop | 3h 22m |
| American | $545 | nonstop | 3h 21m |
Prices checked Oct 12, 2026, 8:22 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 | $988 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights | $501 |
| Trip total for two | $1,489 |
Regular: $1,685 You pay: $1,489 Saved: $196
the typical fare on this route.
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Why go now
At $494 per person ($988 for two), this fare is $98 below the typical fare on this route, a 17% drop, and it's the lowest we've seen in 30 days. Across the 12 offers we checked, fares ran from $494 to $735. The catch is time. The Frontier flight leaves at 12:45 PM on Friday, Oct 16, connects once and lands at 10:39 PM, so you're traveling for 10h 54m. If that's too long, American flies nonstop for $545 per person in 3h 22m. The mid-October weather looks workable: 56°F and overcast Friday with a 60% chance of rain, then a mostly clear 52°F Saturday and a clear 62°F Sunday. That's jacket weather for a river cruise, museums and a deep-dish dinner. Our budget for two comes to $2,009, with $520 of that set aside for spending.
The kind of trip this is
This is a city getaway built around architecture, museums, food and live music, all fit into a short weekend. It suits a couple or a pair of friends who like to walk a lot, eat well and don't mind a sweater. With a late Friday arrival, most of the sightseeing falls on Saturday and Sunday, so the pace is brisk. Pick two or three big things and leave room for a long dinner.
Weather in Chicago, Oct 16–18
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 16 | 56 °F | 46 °F | 60% |
| Sat, Oct 17 | 52 °F | 44 °F | 1% |
| Sun, Oct 18 | 62 °F | 45 °F | 1% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best value at $501 for the 2 nights ($251 a night). That gets you a Standard King Room with a 7.5 review score from 224 reviews. Heads-up: it's by Midway, but the Frontier flight lands at O'Hare. River Hotel is the top-rated pick, scoring 8.3 from 7,928 reviews, at $994 for the stay ($497 a night) for a Small Queen Room. Club Quarters Hotel Central Loop, Chicago scores 8.2 from 5,337 reviews at $917 ($459 a night), which makes it the lower-priced of the two Loop options. The Loop puts architecture, theaters and Millennium Park at your doorstep, which is ideal on a short weekend. All three are room only, with no free cancellation.
Holiday Inn Chicago Midway Airport S by IHG
$501 for 2 nights, two guests · $251 a night
See roomsRiver Hotel
$994 for 2 nights, two guests · $497 a night
See roomsClub Quarters Hotel Central Loop, Chicago
$917 for 2 nights, two guests · $459 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, mostly dry Saturday.
- See the Bean and the fountains in Millennium Park, right in The Loop.
- Eat deep-dish at Lou Malnati's or Pequod's and settle the debate yourselves.
- Spend a few hours at the Art Institute of Chicago, a good plan if it's gray out.
- Hear live blues at Kingston Mines on Saturday night.
- Walk the West Loop's restaurant row on Randolph Street for dinner.
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 Myers | Southwest Florida International (RSW) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 10h 54m (1 stop) |
| Distance | 1,102 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | $988 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | $501 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,009 |
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 Myers to Chicago
| Per person | |
|---|---|
| This trip | $494 per person |
| Lowest in the last 30 days | $494 (Oct 13, 2026) |
| Typical price, last 60 days | $592 |
| Price checks | 6 |
Good to know
- Passport: not needed for US citizens; a government ID is enough.
- Currency: US dollar (USD).
- No passport needed, and you'll pay in US dollars.
- Chicago is 1 hour behind Fort Myers. The Frontier flight takes 10h 54m with one stop and lands at O'Hare (ORD).
- All three hotels are room only and have no free cancellation, so be sure of your dates before you book.
- Prices are all-in, with taxes and fees, as we found them. They can change before you book.
- Pack layers: lows run 44–46°F all weekend.
Questions readers ask
How much is the flight?
When we checked, Frontier was $494 per person round trip, or $988 for two, with taxes and fees included. It has one stop. American flies nonstop for $545 per person.
Do I need a passport?
No. It's a domestic trip from Southwest Florida International (RSW) to Chicago, and you'll pay in US dollars.
What is the weather like?
Friday looks overcast with a high of 56°F and a 60% chance of rain. Saturday is mostly clear at 52°F, and Sunday is clear at 62°F. Lows sit between 44°F and 46°F.
Is 2 nights enough?
For a focused city weekend, yes. The Frontier flight lands at 10:39 PM Friday, so Saturday is your full day. If you want more time, the American nonstop lands at 10:40 AM for $545 per person.
What does the whole weekend cost for two?
Our budget comes to $2,009 for two. That's $988 for flights, $501 for the Holiday Inn near Midway and $520 for spending, or $130 per person per day.
Which airport do I land at?
Both the Frontier and American flights land at Chicago O'Hare International (ORD). The city's other airport is Chicago Midway International (MDW), which is where the Holiday Inn is.
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Image credits
- Photo: K / Pexels, Pexels License
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