Chicago from Fort Myers, Oct 23–25: $1,650 for two, all in
The verdict
Our verdict
Worth it, if
- $479 per person, $121 below the typical fare on this route
- Aloft by Marriott Chicago Mag Mile scores 8.1 from 2,536 reviews
- Highs of 68–72°F and rain chances of 5–12% all weekend
The catch: The $479 Frontier fare has 1 stop and takes 10h 54m, and a checked bag is about $240 for two, which isn't in the total.
Worth it if you'd trade a long travel day for the lower fare; skip it if you'd rather pay $1,108 for two for the 3h 22m American nonstop.
Worth it if you don't mind a long travel day: $1,650 for two covers the flights at $958, the Aloft by Marriott Chicago Mag Mile at $597 and its $95 property fee, with taxes and fees included. The trip runs Oct 23–25, 2026, 2 nights, on Frontier with 1 stop and 10h 54m of travel on the way out. A checked bag and spending money aren't in that total.
The total, before you go
$1,650 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
| For two | |
|---|---|
| Flights for two, round trip | $958 |
| Aloft by Marriott Chicago Mag Mile, 2 nights, two guests, taxes in | $597 |
| Resort fee, collected at the desk | $95 |
| The total, before you go | $1,650 |
| A checked bag each, round trip (not in the total) | about $240 |
$121 per person below the typical fare on this route.
Not in it: seat picks on basic fares and a checked bag (about $60 each way per bag on Frontier, $240 for two round trip); the resort fee is counted above. Prices are what we found at the time shown; the booking site’s checkout is the binding one.
The flight
$479 per person, round trip
$958 for two, taxes and fees included · Frontier · 1 stop · 10h 54m
Out Fri, Oct 23, 12:45 PM – Fri, Oct 23, 10:39 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $479 | 1 stop | 10h 54m |
| American | $554 | nonstop | 3h 22m |
| American | $554 | nonstop | 3h 21m |
Prices checked Oct 16, 2026, 12:54 AM EDT. Prices change; the binding price is the one on the booking site.
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Why now
At $479 per person, this Frontier fare is $121 below the typical fare on this route, 20% under, and it's the lowest in 30 days across the 13 checks we ran. Fares we saw for these dates ran from $479 to $735 per person. The late October forecast for Chicago looks mild: highs of 68–72°F, lows of 58–59°F and rain chances of 5% to 12% under overcast skies. That's good walking weather for the lakefront, Millennium Park and an architecture cruise on the river. Add the Aloft in Streeterville and the whole trip comes to $1,650 for two, all in, when we checked. Plan on spending money on top of that. We budget $520 for two, or $130 per person a day. Prices change, so check the live fare before you commit.
The kind of trip this is
A city long weekend built around food, architecture and music: a river cruise, a world-class museum, deep-dish and a late blues set. It suits a couple or two friends who like to walk and eat their way through a place. The pace is easy, with one full Saturday in the middle, since Friday's flight gets in at 10:39 PM.
Weather in Chicago, Oct 23–25
Highs 68–72°F, little rain expected
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 72 °F | 59 °F | 5% |
| Sat, Oct 24 | 69 °F | 58 °F | 5% |
| Sun, Oct 25 | 68 °F | 58 °F | 12% |
Where to stay in Chicago
Aloft by Marriott Chicago Mag Mile is the best value and the hotel in our total: $597 for the 2 nights ($299 a night), plus a $95 property fee that's already counted, with an 8.1 score from 2,536 reviews. It's in Streeterville, part of Magnificent Mile / Streeterville, which is good for shopping on Michigan Avenue and close to the lakefront. Hampton Inn Chicago West Loop Fulton Market Area is the top rated at 8.8 from 776 reviews: $630 for the stay ($315 a night) with breakfast, plus a $100 property fee. The West Loop puts you near the restaurant row on Randolph Street. Hilton Chicago costs $637 ($319 a night) plus a $101 property fee and scores 7.9 from 982 reviews. It's in The Loop, near Millennium Park and the theaters. None of the three offers free cancellation.
Aloft by Marriott Chicago Mag Mile
$597 for 2 nights, two guests · $299 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
$630 for 2 nights, two guests · $315 a night
See roomsHilton Chicago
$637 for 2 nights, two guests · $319 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
- Eat deep-dish 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
- 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 | $958 |
| Hotel, 2 nights (Aloft by Marriott Chicago Mag Mile) | $597 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $2,075 |
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 | $479 per person |
| Lowest in the last 30 days | $479 (Oct 16, 2026) |
| Typical price, last 60 days | $600 |
| Price checks | 13 |
Good to know
- Passport: no passport needed for travelers from the United States: a government photo ID is enough for Chicago.
- Currency: US dollar (USD).
- No passport needed, and you'll pay in US dollars
- Chicago is 1 hour behind Fort Myers
- The Frontier flight leaves RSW at 12:45 PM, has 1 stop and lands at O'Hare (ORD) at 10:39 PM
- None of the three hotels offers free cancellation
- A checked bag is about $240 for two and isn't in the $1,650 total
Questions readers ask
Is it worth it?
Worth it if a long travel day doesn't bother you. The fare is $479 per person, $121 below the typical fare on this route, and the forecast shows highs of 68–72°F. The trade-off is 1 stop and 10h 54m of travel on the way out.
How much is the whole trip for two?
$1,650 for two, all in, when we checked: flights at $958, the Aloft by Marriott Chicago Mag Mile at $597 and its $95 property fee. Checked bags (about $240 for two) and spending money aren't included. We budget $520 for spending.
Is there a nonstop?
Yes. American has nonstops at $554 per person, $1,108 for two. One leaves at 8:18 AM and takes 3h 22m, and another leaves at 11:54 AM and takes 3h 21m. The Frontier fare is lower, but it has 1 stop.
What is the weather like?
The forecast is overcast and mild: a high of 72°F on Friday, 69°F on Saturday and 68°F on Sunday, with lows of 58–59°F. Rain chances are 5% on Friday and Saturday and 12% on Sunday.
Is 2 nights enough?
It's enough for a long weekend. You land at 10:39 PM on Friday, so Saturday is your full day. That's time for the river cruise, Millennium Park, the Art Institute, deep-dish and a blues set at Kingston Mines.
Do I need a passport?
No. It's a domestic trip, you'll pay in US dollars, and Chicago is 1 hour behind Fort Myers.
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The catch: The $480 fare has two stops and takes 33h 7m out, so Friday night's room sits empty and you get one night in town.
Worth it if you'll pay $537 per person for a one-stop flight that lands Friday morning; skip the $480 fare if you want a real weekend.
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