St. Pete / Clearwater from Chicago, Oct 23–25: round trip from $352
Round-trip flights from Chicago to St. Pete / Clearwater are $352 per person ($704 for two) for Oct 23–25, 2026, a 2-night weekend on Frontier with 1 stop, not nonstop. The forecast shows highs of 85–86°F with a small chance of rain, and the best-value room, at Clearwater Beach Hotel, is $356 for the stay.
The flight
$375 $352 per person, round trip
the typical fare on this route
$704 for two, taxes and fees included · Frontier · 1 stop · 17h 33m
Out Fri, Oct 23, 6:00 AM – Sat, Oct 24, 12:33 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | $352 | 1 stop | 17h 33m |
| United | $505 | nonstop | 5h 49m |
| Frontier | $429 | 2 stops | 22h 13m |
Prices checked Oct 13, 2026, 3:17 AM CDT. 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 |
| Clearwater Beach Hotel, 2 nights | $356 |
| Trip total for two | $1,060 |
Regular: $1,106 You pay: $1,060 Saved: $46
the typical fare on this route.
Tweak this trip
Why go now
At $352 per person, this fare is $23 below the typical fare on this route, which is $375. That's 6% less, and it carries the Lowest in 30 days badge. We checked 12 offers, and fares ran from $352 to $505 per person. Prices are all-in, taxes and fees included, as we found them, and they can change. Late October on the Gulf looks warm: forecast highs of 85–86°F, lows of 74–75°F and rain chances from 16% to 32%. The spring break and spring training crowds that fill the beaches come in March, not October. Heads-up on time, though. The Frontier routing takes 17h 33m and lands at 12:33 AM on Saturday, Oct 24, so think of this as a beach Saturday and Sunday, not a full Friday. If that works for you, it's a warm, good-value getaway from Chicago.
The kind of trip this is
This is a beach weekend first, with a side of culture and food. Calm Gulf water and white sand make it easy for couples or a pair of friends who want sun without much planning. The pace is slow: sand in the morning, maybe a museum or a boat trip in the afternoon, a sunset at the pier at night. Short trips like this one work best when you skip the packed schedule.
Weather in St. Pete / Clearwater, Oct 23–25
Highs 85–86°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri, Oct 23 | 86 °F | 74 °F | 16% |
| Sat, Oct 24 | 85 °F | 75 °F | 19% |
| Sun, Oct 25 | 85 °F | 74 °F | 32% |
Where to stay in St. Pete / Clearwater
All three picks are in Clearwater Beach, which is good for powder-white sand, Pier 60 sunsets and family resorts. Clearwater Beach Hotel is the best value at $356 for the stay ($178 per night), with a 7.6 review score from 2,682 reviews. It's the only one of the three with free cancellation. Barefoot Bay Resort Motel is the top rated at 9.4 from 180 reviews, for $380 for the stay ($190 per night), in a Queen Room with Sofa Bed. Hilton Clearwater Beach Resort & Spa is the 4-star option at $555 for the stay ($278 per night), rated 7.7 from 1,117 reviews, for an Interior Room. All three are room only. If you'd like a quieter beach, St. Pete Beach is the low-key alternative.
Clearwater Beach Hotel
$356 for 2 nights, two guests · $178 a night
See roomsBarefoot Bay Resort Motel
$380 for 2 nights, two guests · $190 a night
See roomsHilton Clearwater Beach Resort & Spa
$555 for 2 nights, two guests · $278 a night
See roomsAll hotels in St. Pete / Clearwater for these dates
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Where in St. Pete / Clearwater
- Clearwater Beach: Powder-white sand, Pier 60 sunsets and family resorts.
- St. Pete Beach: Quieter Gulf beach with the landmark Don CeSar resort.
- Downtown St. Petersburg: Museums, craft breweries and a waterfront pier.
- Indian Rocks Beach: Low-key beach cottages and condos between the two hubs.
What to do in St. Pete / Clearwater
- Catch the nightly sunset festival at Pier 60 in Clearwater Beach.
- See the Salvador Dalí Museum in St. Petersburg.
- Boat out to Caladesi Island State Park for a beach day away from the hotels.
- Kayak the mangroves of Weedon Island Preserve.
- Eat grouper sandwiches at John's Pass Village.
Tours and tickets in St. Pete / Clearwater
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Getting there and around
| Airports in Chicago | Chicago O'Hare International (ORD), Chicago Midway International (MDW) |
|---|---|
| Airports in St. Pete / Clearwater | Tampa International (TPA), St. Pete-Clearwater International (PIE) |
| Flight time | 17h 33m (1 stop) |
| Distance | 999 miles each way |
| Time difference | +1 hour |
What 2 nights in St. Pete / Clearwater costs
| Estimate | |
|---|---|
| Flights for two | $704 |
| Hotel, 2 nights (Clearwater Beach Hotel) | $356 |
| Food, getting around and tickets, 2 days for two | $520 |
| Total for two | $1,580 |
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: Chicago to St. Pete / Clearwater
| Per person | |
|---|---|
| This trip | $352 per person |
| Lowest in the last 30 days | $352 (Oct 13, 2026) |
| Typical price, last 60 days | $375 |
| Price checks | 5 |
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.
- St. Pete / Clearwater is 1 hour ahead of Chicago.
- The $352 Frontier fare leaves O'Hare at 6:00 AM Friday, Oct 23, makes 1 stop and lands in Tampa at 12:33 AM Saturday.
- We also found a United nonstop for $505 per person that takes 5h 49m.
- All three hotels are room only. Clearwater Beach Hotel has free cancellation, the other two don't.
Questions readers ask
How much is the flight?
$352 per person round trip on Frontier, or $704 for two, all-in as we found it. That's $23 below the typical fare on this route of $375. The routing has 1 stop and takes 17h 33m.
Is there a nonstop?
Yes. We found a United nonstop for $505 per person ($1,010 for two). It leaves at 12:59 PM on Oct 23, lands at 4:47 PM, and takes 5h 49m. That's $153 more per person than the Frontier fare, but you get Friday evening on the beach.
Do I need a passport?
No. It's a domestic trip from Chicago to Tampa, about 999 miles, and the currency is the US dollar.
What is the weather like?
The forecast shows highs of 85–86°F and lows of 74–75°F. Friday and Saturday look partly cloudy with rain chances of 16% and 19%. Sunday looks clear, with a 32% chance of rain.
Is 2 nights enough?
For a beach reset, yes, but on the Frontier fare you land at 12:33 AM Saturday, so you really get Saturday and Sunday. Our budget for two comes to $1,580: $704 for flights, $356 for the hotel and $520 for spending.
Which hotel lets me cancel for free?
Clearwater Beach Hotel, at $356 for the stay. Barefoot Bay Resort Motel ($380) and Hilton Clearwater Beach Resort & Spa ($555) didn't offer free cancellation when we checked.
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St. Pete / Clearwater in pictures
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Image credits
- Photo: Jeffrey Eisen / Pexels, Pexels License
- Photo: Miriam Salgado / Pexels, Pexels License
- Photo: Solvej Nielsen / Pexels, Pexels License