Chicago from Tampa, 23 – 25 Oct: £924 for two, all in
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The verdict
Our verdict
Worth it, if
- Fare $352 per person, $29 below the typical fare on this route
- Hilton Chicago in The Loop, 7.9 from 981 reviews, $261 a night
- Highs of 76°F, 72°F and 57°F, rain chance 33% or less
The catch: The Frontier fare has one stop and the flight up takes 6h 41m, and a checked bag is about $240 for two, not in the total.
Worth it if you pack light and want a Loop weekend of museums and food; skip it if you'd rather pay more to fly nonstop.
Worth it if you can live with a stop: Chicago from Tampa is $1,226 for two, with the Frontier flights at $704 and 2 nights at Hilton Chicago at $522, taxes and fees included. You fly out Friday, Oct 23 and come home Sunday, Oct 25, 2026, and the Frontier fare has one stop, not a nonstop. A checked bag, any resort fee and spending money aren't in that total.
The total, before you go
£924 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £531 |
| Hilton Chicago, 2 nights, two guests, taxes in | £393 |
| The total, before you go | £924 |
| Hold luggage each, return (not in the total) | about £181 |
£22 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
£265 per person, return
£531 for two, taxes and fees included · Frontier · 1 stop · 6h 41m
Out Fri, Oct 23, 12:50 PM – Fri, Oct 23, 6:31 PM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £265 | 1 stop | 6h 41m |
| American | £355 | nonstop | 3h 6m |
| Frontier | £331 | 2 stops | 22h 28m |
Prices checked 12 Oct 2026, 14:38 GMT-4. Prices change; the binding price is the one on the booking site.
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Why now
At $352 per person, the Frontier fare is $29 below the typical fare on this route, which is $381. That's 8% less, and it's the lowest fare we've seen in 30 days. Across the 12 offers we checked, fares ran from $352 to $481 per person. The American nonstop was $471 per person, so you save by taking the stop. In late October you get a city weekend in mild fall weather. Friday is overcast with a high of 76°F, Saturday brings drizzle and a high of 72°F, and Sunday cools to 57°F. Rain chances run between 19% and 33%. Two nights gives you time for the river cruise, the Art Institute and a deep-dish dinner. Prices are all-in as we found them and can change before you book.
The kind of trip this is
This is a quick city break built around architecture, museums and food. It suits a couple or two friends who like to walk, eat well and stay out for live music. The pace is steady: the river cruise and Millennium Park on Saturday, then the Art Institute and a deep-dish lunch on Sunday before the flight home. It's not a beach trip or a rest-and-recharge trip.
Weather in Chicago, 23 – 25 Oct
Highs 57–76°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 76 °F | 67 °F | 33% |
| Sat 24 Oct | 72 °F | 50 °F | 23% |
| Sun 25 Oct | 57 °F | 49 °F | 19% |
Where to stay in Chicago
Hilton Chicago is the best-value pick and the hotel in the total: $522 for the 2 nights ($261 a night) for a King Room, rated 7.9 from 981 reviews. It's in The Loop, with architecture, theatres and Millennium Park right outside. Hampton Inn Chicago West Loop Fulton Market Area is the top-rated pick at 8.8 from 769 reviews and includes breakfast. It costs $683 for the stay ($342 a night) and sits in the West Loop, the converted-warehouse neighborhood with the restaurant row on Randolph Street. Congress Plaza Hotel Chicago, also in The Loop, costs $550 ($275 a night) and is rated 7.1 from 4,544 reviews. It's the only one of the three with free cancellation.
Hilton Chicago
£393 for 2 nights, two guests · £197 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
£515 for 2 nights, two guests · £258 a night
See roomsCongress Plaza Hotel Chicago
£415 for 2 nights, two guests · £207 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, steps from The Loop hotels
- Eat deep-dish at Lou Malnati's or Pequod's
- Spend Sunday morning at the Art Institute of Chicago
- Hear live blues at Kingston Mines on Saturday night
- Catch a Cubs game at Wrigley Field if one is on
Also worth it
- Visit the Art Institute of Chicago
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Getting there and around
| Airports in Tampa | Tampa International (TPA), St. Pete-Clearwater International (PIE) |
|---|---|
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
| Flight time | 6h 41m (1 stop) |
| Distance | 1,006 miles each way |
| Time difference | -1 hour |
What 2 nights in Chicago costs
| Estimate | |
|---|---|
| Flights for two | £531 |
| Hotel, 2 nights (Hilton Chicago) | £393 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,316 |
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: Tampa to Chicago
| Per person | |
|---|---|
| This trip | £265 per person |
| Lowest in the last 30 days | £265 (12 Oct 2026) |
| Typical price, last 60 days | £287 |
| 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 you pay in US dollars
- Chicago is 1 hour behind Tampa
- Frontier leaves TPA at 12:50 PM and lands at ORD at 6:31 PM, with one stop
- A checked bag is about $240 for two and isn't in the $1,226 total
- Only Congress Plaza Hotel Chicago offers free cancellation; the other two rates don't
Questions readers ask
Is it worth it?
For travelers who pack light and don't mind a stop, yes. The fare is $29 below the typical fare on this route, and $1,226 covers flights and 2 nights in The Loop for two. If a 6h 41m trip up with one stop sounds like too much, look at the American nonstop instead.
How much is the whole trip for two?
It's $1,226, all in: $704 for the Frontier flights and $522 for 2 nights at Hilton Chicago, taxes and fees included. We budget $130 per person per day for spending, which adds $520 and brings the trip to $1,746. A checked bag is about $240 for two on top of that.
Is there a nonstop?
Yes. When we checked, American had a nonstop that leaves at 1:53 PM and lands at 3:59 PM, a 3h 6m flight, for $471 per person, or $942 for two. Our pick is the Frontier fare at $352 per person, which has one stop.
What is the weather like?
The forecast has Friday overcast at 67°F to 76°F with a 33% chance of rain. Saturday brings drizzle at 50°F to 72°F with a 23% chance, and Sunday is overcast at 49°F to 57°F with a 19% chance. Pack a light jacket.
Do I need a passport?
No. It's a domestic trip from Tampa to Chicago O'Hare, and you pay in US dollars.
Is 2 nights enough?
For a first taste of the city, yes. You land at 6:31 PM Friday, so you'll have time for deep-dish that night. Saturday covers the river cruise, Millennium Park and blues at Kingston Mines, and the Art Institute fits on Sunday.
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£770 for two · 2 nights · flights, hotel, taxes, fees & the resort fee
Flights £479 + hotel £261 + resort fee £30, taxes in · a checked bag each adds about £121
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The catch: One stop each way adds up to 40h 36m of travel, so you land Saturday afternoon and pay for a hotel night you never use.
Worth it if you can take Monday off and are happy with one short day in town; skip it if you want a full weekend.
All trips from Tampa · Chicago from every city · Prices on this route · Trips in October 2026 · Home
Chicago in pictures
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Prices converted from US dollars at the rate of 15 Oct 2026.
Image credits
- Photo: Joshua Santos / Pexels, Pexels License
- Photo: K / Pexels, Pexels License
- Photo: Mik Dominguez / Pexels, Pexels License