$44 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, Aug 10 - Thu, Aug 14
TPA
Tampa Intl.
MDW
Midway Intl.
$330 Roundtrip, found 1 day ago
$330
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Aug 10 from Tampa Intl. to Midway Intl., returning Thu, Aug 14, priced at $330 found 1 day ago
Sat, Aug 9 - Wed, Aug 13
TPA
Tampa Intl.
ORD
O'Hare Intl.
$365 Roundtrip, just found
$365
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Aug 9 from Tampa Intl. to O'Hare Intl., returning Wed, Aug 13, priced at $365 just found
Sat, Aug 9 - Sat, Aug 16
SRQ
Sarasota-Bradenton Intl.
MDW
Midway Intl.
$693 Roundtrip, found 2 days ago
$693
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 9 from Sarasota-Bradenton Intl. to Midway Intl., returning Sat, Aug 16, priced at $693 found 2 days ago
Sat, Aug 9 - Mon, Aug 11
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$727 Roundtrip, just found
$727
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 9 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Mon, Aug 11, priced at $727 just found

Airfares from $44 One Way, $87 Round Trip from St. Petersburg - Clearwater to Chicago

Prices starting at $87 for return flights and $44 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.

Sat, Sep 6 - Wed, Sep 10
TPA
Tampa
ORD
Chicago
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Sep 6 from Tampa to Chicago, returning Wed, Sep 10, priced at $87 just found
Fri, Sep 5 - Sun, Sep 7
TPA
Tampa
MDW
Chicago
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Sep 5 from Tampa to Chicago, returning Sun, Sep 7, priced at $101 found 1 day ago
Wed, Oct 15 - Tue, Oct 28
TPA
Tampa
ORD
Chicago
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select United flight, departing Wed, Oct 15 from Tampa to Chicago, returning Tue, Oct 28, priced at $139 found 1 day ago
Wed, Oct 15 - Tue, Oct 28
TPA
Tampa
ORD
Chicago
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 15 from Tampa to Chicago, returning Tue, Oct 28, priced at $139 found 1 day ago
Tue, Dec 16 - Tue, Dec 30
SRQ
Sarasota
ORD
Chicago
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Dec 16 from Sarasota to Chicago, returning Tue, Dec 30, priced at $140 found 1 day ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Stella Hotel & Ballroom
3.5-star property

The Stella Hotel & Ballroom

9.4/10 Exceptional! (1,006 reviews)

Sep 15 - Sep 21

6 night stay

Tampa (TPA) to Chicago (CHI)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 14 hours ago
Stayed in Kenosha for one night. Picked Stella at random. What a great place for a great price. So nice. So clean. Great hotel with great staff

Reviewed on Apr 15, 2025

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (255 reviews)

Sep 15 - Sep 21

6 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 14 hours ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,270 reviews)

Sep 12 - Sep 14

2 night stay

Tampa (TPA) to Chicago (ORD)

United • Coach

Chicago (ORD) to Tampa (TPA)

Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Very convenient to the heart of Chicago! Nice hotel!

Reviewed on Jul 24, 2025

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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
1013 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Austrian, Emirates, Copa Airlines, Air New Zealand, Swiss, United Airlines, Alaska Airlines, Frontier Airlines, Qantas, Royal Jordanian, ANA, Brussels Airlines, Lufthansa, Spirit Airlines, Gulf Air, British Airways
Earliest Flight Arrival
1:06PM UTC
Latest Flight Arrival
1:00AM UTC

St. Petersburg - Clearwater to Chicago

Planning a trip is rarely straight forward, especially when searching for cheap deals. At Orbitz.com, we make it easier than anywhere else by providing you with guaranteed low prices. So if you are looking for St. Petersburg - Clearwater to Chicago flights at low cost, you will not be disappointed.

Cruising for a bargain deal

Regardless of your destination, we always provide you fantastic bargains for your trip, and that includes on hotels and even cruises. We offer budget air fares on flights from St. Petersburg - Clearwater to Chicago so you can reach your destination with more money in your pocket to spend.

Cheap St. Petersburg - Clearwater to Chicago flights that lead to rewards

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Quality combinations

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Even last minute bookings on our apps

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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.

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.