Chicago from Fort Myers, 16 – 18 Oct: £1,122 for two, all in
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The verdict
Our verdict
Worth it, if
- $494 per person, $98 below the typical fare on this route
- Saturday and Sunday forecast: 1% rain chance, highs 52°F and 62°F
- River Hotel in The Loop scores 8.3 from 7,928 reviews
The catch: The Frontier fare has 1 stop and takes 10h 54m, landing at 10:39 PM, while the American nonstop costs $545 per person.
Worth it if a long Friday travel day is fine for $98 per person saved; skip it if Friday evening in the city matters to you.
Worth it if you can live with a stop: $1,489 for two covers the Frontier flights at $988 plus the hotel at $501 for 2 nights, taxes and fees included. You'd go Oct 16–18, 2026, Friday to Sunday, and the outbound has 1 stop and takes 10h 54m. Resort fees, a checked bag and spending money are not in the total.
The total, before you go
£1,122 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £745 |
| Holiday Inn Chicago Midway Airport S by IHG, 2 nights, two guests, taxes in | £378 |
| The total, before you go | £1,122 |
| Hold luggage each, return (not in the total) | about £181 |
£74 per person below the typical fare on this route.
Not in it: seat selection on basic fares and hold luggage (about £45 each way per bag on Frontier, £181 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
£372 per person, return
£745 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 | £372 | 1 stop | 10h 54m |
| American | £411 | nonstop | 3h 22m |
| American | £411 | nonstop | 3h 21m |
Prices checked 12 Oct 2026, 20:22 GMT-4. Prices change; the binding price is the one on the booking site.
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Tweak this trip
Why now
The Frontier fare is $494 per person, $98 below the typical fare on this route, or 17% under it, and it's the lowest in 30 days of our checks. Across 12 offers we saw fares from $494 to $735 per person. That puts the whole trip at $1,489 for two with the best-value hotel, before resort fees, a checked bag and spending money; our budget adds $520 for spending, $2,009 in all. The weather lines up for the part that counts: Friday is overcast with a 60% rain chance, but Saturday is mostly clear at 52°F and Sunday is clear at 62°F, each with a 1% chance of rain. Mid-October is jacket weather, good for walking the river and the museums. Prices were all-in when we checked and can change.
The kind of trip this is
A city weekend built on architecture, museums, deep-dish and live blues. It suits a couple or two friends who like to walk, eat well and stay out late. The pace is brisk: you land Friday night, so Saturday and Sunday do the work. Pack layers, since lows run 44°F to 46°F.
Weather in Chicago, 16 – 18 Oct
Highs 52–62°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 16 Oct | 56 °F | 46 °F | 60% |
| Sat 17 Oct | 52 °F | 44 °F | 1% |
| Sun 18 Oct | 62 °F | 45 °F | 1% |
Where to stay in Chicago
Holiday Inn Chicago Midway Airport S by IHG is the best-value pick and the one in our total: $501 for 2 nights in a Standard King Room, $251 a night, scored 7.5 from 224 reviews. As the name says, it sits by Midway airport, away from the center, and the flight lands at O'Hare. Club Quarters Hotel Central Loop, Chicago is $917 for the stay, $459 a night, scored 8.2 from 5,337 reviews. River Hotel is the top rated at 8.3 from 7,928 reviews, $994 for the stay, $497 a night. Both of those are in The Loop, with architecture, theatres and Millennium Park at your doorstep. None of the three offers free cancellation, and all are room only.
Holiday Inn Chicago Midway Airport S by IHG
£378 for 2 nights, two guests · £189 a night
See roomsRiver Hotel
£749 for 2 nights, two guests · £375 a night
See roomsClub Quarters Hotel Central Loop, Chicago
£691 for 2 nights, two guests · £346 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
- See the Bean and the fountains in Millennium Park
- 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
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 | £745 |
| Hotel, 2 nights (Holiday Inn Chicago Midway Airport S by IHG) | £378 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,514 |
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 | £372 per person |
| Lowest in the last 30 days | £372 (13 Oct 2026) |
| Typical price, last 60 days | £446 |
| Price checks | 6 |
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 the currency is the US dollar
- Chicago is 1 hour behind Fort Myers
- The Frontier flight leaves RSW at 12:45 PM and lands at O'Hare at 10:39 PM, 1 stop
- The route covers 1,102 miles; Chicago also has Midway International (MDW)
- None of the three hotels offers free cancellation
Questions readers ask
Is it worth it?
Worth it if you don't mind a stop. The fare is $494 per person, 17% under the typical fare on this route, and the weekend forecast is dry. The trade-off is a 10h 54m outbound on Frontier.
How much is the whole trip for two?
$1,489 for two, taxes and fees included: $988 for the Frontier flights and $501 for 2 nights at Holiday Inn Chicago Midway Airport S by IHG. Resort fees, a checked bag and spending money are not in it; our budget suggests $520 for spending.
Is there a nonstop?
Yes. American flies nonstop at $545 per person, $1,090 for two, with departures at 8:18 AM and 11:54 AM that take about 3h 22m and 3h 21m.
What is the weather like?
Friday is overcast, 56°F, with a 60% chance of rain. Saturday is mostly clear at 52°F and Sunday is clear at 62°F, both with a 1% chance of rain. Lows sit between 44°F and 46°F.
Is 2 nights enough?
For a first look, yes. You land Friday at 10:39 PM, so plan Saturday and Sunday around the river cruise, Millennium Park, the Art Institute and deep-dish.
Do I need a passport?
No. It's a domestic trip, prices are in US dollars, and Chicago is 1 hour behind Fort Myers.
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License
- Photo: Joshua Santos / Pexels, Pexels License