Chicago from Tampa, Oct 23–25: round trip from $352
Round-trip flights from Tampa to Chicago cost $352 per person ($704 for two) all-in on Frontier for Oct 23–25, 2026, a 2-night weekend with 1 stop each way. Highs run 57–76°F with a small chance of rain. The best-value hotel, Hilton Chicago in the Loop, is $522 for the stay.
The flight
$381 $352 per person, round trip
the typical fare on this route
$704 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 | $352 | 1 stop | 6h 41m |
| American | $471 | nonstop | 3h 6m |
| Frontier | $439 | 2 stops | 22h 28m |
Prices checked Oct 12, 2026, 2:38 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 | $704 |
| Hilton Chicago, 2 nights | $522 |
| Trip total for two | $1,226 |
Regular: $1,284 You pay: $1,226 Saved: $58
the typical fare on this route.
Tweak this trip
Why go now
$352 per person round trip, all-in when we checked, which is $29 below the typical fare on this route, or 8% under $381. The fare also carries the Lowest in 30 days badge: across the 12 offers we saw, prices ran from $352 to $481. For two, flights come to $704, and with Hilton Chicago at $522 plus $520 in spending money, the weekend lands at $1,746 for two. Late October is mild going on cool: Friday reaches 76°F, Saturday 72°F with some drizzle, and Sunday drops to 57°F. That's good weather for river walks, museums and long dinners. Prices move, so take these as what we found today, not a promise they'll hold.
The kind of trip this is
This is a city weekend built around food, architecture, museums and live music. It suits a couple or a couple of friends who like to walk, eat well and stay out a little late. The pace is easy but full: one big sight in the morning, deep-dish or a West Loop dinner at night, blues after that. With 2 nights, you pick a neighborhood and settle in.
Weather in Chicago, Oct 23–25
Highs 57–76°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 76 °F | 67 °F | 33% |
| Sat, Oct 24 | 72 °F | 50 °F | 23% |
| Sun, Oct 25 | 57 °F | 49 °F | 19% |
Where to stay in Chicago
Hilton Chicago is the best value at $522 for the 2 nights ($261 a night), with a 7.9 review score from 981 reviews. It's room only and not refundable. Hampton Inn Chicago West Loop Fulton Market Area is the top rated at 8.8 from 769 reviews, $683 for the stay ($342 a night), and breakfast is included. Congress Plaza Hotel Chicago is our budget pick at $550 ($275 a night), rated 7.1 from 4,544 reviews, and it's the only one of the three with free cancellation. Two of the three sit in The Loop, which puts architecture, theatres and Millennium Park at your doorstep. The West Loop is the food pick, with converted warehouses and the restaurant row on Randolph Street.
Hilton Chicago
$522 for 2 nights, two guests · $261 a night
See roomsHampton Inn Chicago West Loop Fulton Market Area
$683 for 2 nights, two guests · $342 a night
See roomsCongress Plaza Hotel Chicago
$550 for 2 nights, two guests · $275 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 and compare notes.
- Spend a morning at the Art Institute of Chicago, handy on Sunday's cooler 57°F day.
- Hear live blues at Kingston Mines on Saturday night.
- Walk Lincoln Park for 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 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 | $704 |
| Hotel, 2 nights (Hilton Chicago) | $522 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,746 |
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 | $352 per person |
| Lowest in the last 30 days | $352 (Oct 12, 2026) |
| Typical price, last 60 days | $381 |
| 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 the currency is the US dollar.
- Chicago is 1 hour behind Tampa.
- The Frontier flight leaves TPA at 12:50 PM on Friday, Oct 23 and lands at O'Hare (ORD) at 6:31 PM, a 6h 41m trip with 1 stop.
- Only Congress Plaza Hotel Chicago offers free cancellation; the other two hotels are non-refundable.
- Prices include taxes and fees as found when we checked, and they can change.
Questions readers ask
How much is the flight?
$352 per person round trip on Frontier, or $704 for two, all-in when we checked. That's $29 below the typical fare on this route of $381.
Is there a nonstop?
Yes. American flies nonstop for $471 per person, leaving at 1:53 PM and landing at 3:59 PM, a 3h 6m trip. The Frontier fare has 1 stop and takes 6h 41m.
What is the weather like?
The forecast shows 76°F and overcast on Friday, 72°F with drizzle on Saturday, and 57°F and overcast on Sunday. Lows run from 49°F to 67°F, so pack a jacket.
Do I need a passport?
No. It's a domestic trip, so a standard ID works, and you'll pay in US dollars.
Is 2 nights enough?
For a first look, yes. You land Friday at 6:31 PM, which leaves a full Saturday for the river cruise, Millennium Park and blues, plus Sunday for the Art Institute.
What does the whole weekend cost?
We figure $1,746 for two: $704 in flights, $522 at Hilton Chicago, and $520 for spending, about $130 per person a day.
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Image credits
- Photo: Joshua Santos / Pexels, Pexels License
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- Photo: Mik Dominguez / Pexels, Pexels License