$48 Cheap flight deals from St. Petersburg - Clearwater (TPA) to Chicago (CHI)

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This Weekend's Flight Deals from St. Petersburg - Clearwater to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Sep 6 - Thu, Sep 10
SRQ
Sarasota-Bradenton Intl.
RFD
Greater Rockford
$164 Roundtrip, found 19 hours ago
$164
Roundtrip
found 19 hours ago
Select Allegiant Air flight, departing Sun, Sep 6 from Sarasota-Bradenton Intl. to Greater Rockford, returning Thu, Sep 10, priced at $164 found 19 hours ago
Fri, Sep 4 - Mon, Oct 5
PIE
St. Petersburg-Clearwater Intl.
RFD
Greater Rockford
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Sep 4 from St. Petersburg-Clearwater Intl. to Greater Rockford, returning Mon, Oct 5, priced at $251 found 1 day ago
Sun, Sep 6 - Thu, Sep 10
TPA
Tampa Intl.
ORD
O'Hare Intl.
$275 Roundtrip, found 4 hours ago
$275
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Sep 6 from Tampa Intl. to O'Hare Intl., returning Thu, Sep 10, priced at $275 found 4 hours ago
Sat, Sep 5 - Tue, Sep 8
TPA
Tampa Intl.
MDW
Midway Intl.
$278 Roundtrip, found 1 day ago
$278
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Tampa Intl. to Midway Intl., returning Tue, Sep 8, priced at $278 found 1 day ago

Airfares from $48 One Way, $108 Round Trip from St. Petersburg - Clearwater to Chicago

Prices starting at $108 for return flights and $48 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 15 - Mon, Jan 18
PIE
St. Petersburg
RFD
Rockford
$108 Roundtrip, found 8 hours ago
$108
Roundtrip
found 8 hours ago
Select Allegiant Air flight, departing Fri, Jan 15 from St. Petersburg to Rockford, returning Mon, Jan 18, priced at $108 found 8 hours ago
Thu, Jan 14 - Sun, Jan 24
SRQ
Sarasota
RFD
Rockford
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Jan 14 from Sarasota to Rockford, returning Sun, Jan 24, priced at $122 found 1 day ago
Tue, Dec 1 - Mon, Dec 7
TPA
Tampa
ORD
Chicago
$149 Roundtrip, just found
$149
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Dec 1 from Tampa to Chicago, returning Mon, Dec 7, priced at $149 just found
Sat, Sep 26 - Wed, Oct 7
TPA
Tampa
MDW
Chicago
$198 Roundtrip, found 4 hours ago
$198
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Tampa to Chicago, returning Wed, Oct 7, priced at $198 found 4 hours ago
Thu, Oct 1 - Sat, Oct 3
TPA
Tampa
RFD
Rockford
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Oct 1 from Tampa to Rockford, returning Sat, Oct 3, priced at $208 found 5 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (556 reviews)

Oct 20 - Oct 27

7 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,386, price is now $1,414 per person
$1,414
per person
found 1 day ago
Loved the hotel, super nice and clean! Felt like home away from home!

Reviewed on Sep 1, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,106 reviews)

Oct 20 - Oct 27

7 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,472, price is now $1,417 per person
$1,417
per person
found 1 day ago
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!

Reviewed on Sep 2, 2026

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9.2/10 Wonderful! (520 reviews)

Oct 20 - Oct 27

7 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,524, price is now $1,591 per person
$1,591
per person
found 1 day ago

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More About Flying To Chicago from St. Petersburg - Clearwater

Route Information for Flights from St. Petersburg - Clearwater to Chicago

Origin Airport IATA Code
TPA
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

St. Petersburg - Clearwater to Chicago

The best fares for St. Petersburg - Clearwater to Chicago flights are always found on Orbitz. With superior discounts and the latest innovations in mobile access, your ideal trip starts with Orbitz.

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Frequently asked questions

Are there non-stop flights from St. Petersburg - Clearwater to Chicago?
Yes, you can book direct flights from Tampa Airport to ORD. What's more, there are 5 airlines for you to choose from. Pretty cool, huh? Find out which of these sought-after carriers meets your needs:

  • United Airlines
  • American Airlines
  • Spirit Airlines
  • Frontier Airlines
  • Southwest Airlines

What is the shortest flight from St. Petersburg - Clearwater to Chicago?
The shortest flight time from St. Petersburg - Clearwater to Chicago is 3 hours and 25 minutes, which gives you ample time to enjoy a beverage or lose yourself in a good book.
What airlines fly from St. Petersburg - Clearwater to Chicago most frequently?
These are the airlines offering the most frequent flights from Tampa, FL (TPA-Tampa Intl.) to Chicago, IL (ORD-O'Hare Intl.). Reserve a seat with one of the following and see why they are the most popular: United Airlines - (UA) with 112 flights every month American Airlines - (AA) with 65 flights every month Spirit Airlines - (NK) with 30 flights every month Frontier Airlines - (F9) with 21 flights every month
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.