St. Pete / Clearwater from Chicago, 23 – 25 Oct: £799 for two, all in
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The verdict
Our verdict
Worth it, if
- Frontier at $352 per person, $23 below the typical fare
- Gulf highs of 85–86°F with rain chances of 16–32%
- Clearwater Beach Hotel, 7.6 from 2,682 reviews, free cancellation
The catch: With one stop on Frontier, the outbound takes 17h 33m and lands at 12:33 AM Saturday, so Friday of a 2-night weekend goes to travel.
Worth it if you'll trade a long Friday of travel for a warm beach Saturday; skip it if every hour of the weekend counts.
Worth it if you don't mind a long travel day: $1,060 for two covers the Frontier flights at $704 plus 2 nights at Clearwater Beach Hotel at $356, with taxes and fees included. The trip runs Oct 23–25, 2026, and the outbound is not nonstop. It has one stop, leaving O'Hare at 6:00 AM Friday and landing in Tampa at 12:33 AM Saturday, and resort fees, a checked bag and spending money are not in the total.
The total, before you go
£799 for two · 2 nights · flights, hotel, taxes & fees
| For two | |
|---|---|
| Flights for two, return | £531 |
| Clearwater Beach Hotel, 2 nights, two guests, taxes in | £268 |
| The total, before you go | £799 |
| Hold luggage each, return (not in the total) | about £181 |
£17 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 · 17h 33m
Out Fri, Oct 23, 6:00 AM – Sat, Oct 24, 12:33 AM
| Airline | Per person | Stops | Duration |
|---|---|---|---|
| Frontier | £265 | 1 stop | 17h 33m |
| United | £381 | nonstop | 5h 49m |
| Frontier | £323 | 2 stops | 22h 13m |
Prices checked 13 Oct 2026, 03:17 GMT-5. Prices change; the binding price is the one on the booking site.
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Why now
At $352 per person, this Frontier fare is $23 below the typical fare on this route, or 6% under, and it's the lowest in 30 days. For two, that's $704 in flights, or $1,060 with 2 nights at Clearwater Beach Hotel, with taxes and fees included. Late October on the Gulf is still warm. The forecast shows highs of 85–86°F, lows of 74–75°F and rain chances of 16% Friday, 19% Saturday and 32% Sunday. The March crowds from spring break and spring training are months away. The trade-off is time, because the low fare takes 17h 33m with one stop. United flies nonstop the same day for $505 per person, or $1,010 for two, and lands at 4:47 PM Friday if you'd rather pay more for the extra evening. Either way, you get two nights by calm Gulf water.
The kind of trip this is
This is a quick beach weekend with calm Gulf water and sugar-white sand. Downtown St. Petersburg's museums and food scene are a short drive away. The pace is slow on purpose: a swim, a grouper sandwich, a Pier 60 sunset, then the same again tomorrow. It suits a couple or two friends who want warm water and an easy rhythm more than a packed itinerary.
Weather in St. Pete / Clearwater, 23 – 25 Oct
Highs 85–86°F, a small chance of rain
| Day | High | Low | Rain chance |
|---|---|---|---|
| Fri 23 Oct | 86 °F | 74 °F | 16% |
| Sat 24 Oct | 85 °F | 75 °F | 19% |
| Sun 25 Oct | 85 °F | 74 °F | 32% |
Where to stay in St. Pete / Clearwater
All three picks are on Clearwater Beach, which is known for powder-white sand, Pier 60 sunsets and family resorts. Clearwater Beach Hotel is the best value at $356 for the 2 nights ($178 a night), with a 7.6 from 2,682 reviews. It's the only one of the three with free cancellation, and it's the hotel in our $1,060 total. Barefoot Bay Resort Motel is the top rated at 9.4 from 180 reviews, at $380 for the stay ($190 a night), with no free cancellation. Hilton Clearwater Beach Resort & Spa is the four-star option at $555 for the stay ($278 a night), rated 7.7 from 1,117 reviews, and it also has no free cancellation. If you'd rather be near museums, craft breweries and a waterfront pier, Downtown St. Petersburg is the base for that.
Clearwater Beach Hotel
£268 for 2 nights, two guests · £134 a night
See roomsBarefoot Bay Resort Motel
£286 for 2 nights, two guests · £143 a night
See roomsHilton Clearwater Beach Resort & Spa
£418 for 2 nights, two guests · £210 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 on Clearwater Beach
- See the Salvador Dalí Museum in St. Petersburg
- Boat out to Caladesi Island State Park for a quieter stretch of sand
- 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 | £531 |
| Hotel, 2 nights (Clearwater Beach Hotel) | £268 |
| Food, getting around and tickets, 2 days for two | £392 |
| Total for two | £1,191 |
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 | £265 per person |
| Lowest in the last 30 days | £265 (13 Oct 2026) |
| Typical price, last 60 days | £283 |
| Price checks | 5 |
Good to know
- Passport: no passport needed for travellers from the United States: a government photo ID is enough for St. Pete / Clearwater.
- Currency: US dollar (USD).
- No passport needed, you pay in US dollars, and Florida is 1 hour ahead of Chicago.
- The outbound flight on Frontier leaves ORD at 6:00 AM Friday and reaches TPA at 12:33 AM Saturday, with one stop.
- Of the three hotels, only Clearwater Beach Hotel offers free cancellation, and all three are room only.
- Prices are all-in as found when we checked, and they can change before you book.
- Spring break and spring training baseball fill the beaches in March, so October avoids that.
Questions readers ask
Is it worth it?
It's worth it if you're fine with a long Friday. The fare is $23 per person below the typical fare on this route and the forecast shows highs of 85–86°F, but with one stop the outbound takes 17h 33m.
How much is the whole trip for two?
It's $1,060 for two with taxes and fees included: $704 for the Frontier flights plus $356 for 2 nights at Clearwater Beach Hotel. Resort fees, a checked bag and spending money are not in that total.
Is there a nonstop?
Yes. United flies nonstop on Friday, Oct 23, leaving at 12:59 PM and landing at 4:47 PM, for $505 per person, or $1,010 for two in flights alone.
What is the weather like?
The forecast shows highs of 86°F Friday and 85°F on Saturday and Sunday, with lows of 74–75°F. Friday and Saturday look partly cloudy with rain chances of 16% and 19%, and Sunday looks clear with a 32% chance.
Is 2 nights enough?
On the Frontier fare you land at 12:33 AM Saturday, so you get one full beach day plus part of Sunday. Return flight times are not in our data, so check them before you book.
Do I need a passport?
No, it's a domestic trip. You'll pay in US dollars, and Florida is 1 hour ahead of Chicago.
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St. Pete / Clearwater in pictures
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Prices converted from US dollars at the rate of 15 Oct 2026.
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