$49 Cheap flight deals from St. Petersburg - Clearwater (TPA) to Chicago (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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.

Sat, Jul 5 - Fri, Aug 8
TPA
Tampa Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 4 hours ago
$172
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Jul 5 from Tampa Intl. to O'Hare Intl., returning Fri, Aug 8, priced at $172 found 4 hours ago
Fri, Jul 4 - Thu, Jul 10
TPA
Tampa Intl.
MDW
Midway Intl.
$222 Roundtrip, found 4 hours ago
$222
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Jul 4 from Tampa Intl. to Midway Intl., returning Thu, Jul 10, priced at $222 found 4 hours ago
Sun, Jul 6 - Sat, Jul 12
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$501 Roundtrip, found 3 days ago
$501
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Jul 6 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Sat, Jul 12, priced at $501 found 3 days ago
Sat, Jul 5 - Thu, Jul 10
SRQ
Sarasota-Bradenton Intl.
MDW
Midway Intl.
$555 Roundtrip, found 3 days ago
$555
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jul 5 from Sarasota-Bradenton Intl. to Midway Intl., returning Thu, Jul 10, priced at $555 found 3 days ago

Airfares from $49 One Way, $94 Round Trip from St. Petersburg - Clearwater to Chicago

Prices starting at $94 for return flights and $49 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.

Wed, Jul 23 - Mon, Aug 11
TPA
Tampa
ORD
Chicago
$94 Roundtrip, found 17 hours ago
$94
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Wed, Jul 23 from Tampa to Chicago, returning Mon, Aug 11, priced at $94 found 17 hours ago
Tue, Jul 22 - Tue, Jul 29
TPA
Tampa
ORD
Chicago
$95 Roundtrip, found 1 day ago
$95
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 22 from Tampa to Chicago, returning Tue, Jul 29, priced at $95 found 1 day ago
Fri, Sep 19 - Mon, Sep 22
TPA
Tampa
MDW
Chicago
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Sep 19 from Tampa to Chicago, returning Mon, Sep 22, priced at $98 just found
Thu, Sep 4 - Sun, Sep 7
TPA
Tampa
ORD
Chicago
$98 Roundtrip, found 4 hours ago
$98
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Tampa to Chicago, returning Sun, Sep 7, priced at $98 found 4 hours ago
Thu, Sep 18 - Tue, Sep 23
TPA
Tampa
MDW
Chicago
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Sep 18 from Tampa to Chicago, returning Tue, Sep 23, priced at $157 found 2 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
4.0-star property

Palmer House a Hilton Hotel

8.4/10 Very Good! (1,755 reviews)

Aug 20 - Aug 24

4 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Old school, nice and clean

Reviewed on Jun 21, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,623 reviews)

Aug 20 - Aug 24

4 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,769 reviews)

Aug 20 - Aug 24

4 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Fantastic stay, amazing location.

Reviewed on Jun 25, 2025

Don't see what you're looking for?
See all available trips from St. Petersburg - Clearwater to Chicago
View all trips

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

Find bargain tickets for flights from St. Petersburg - Clearwater to Chicago, and plan your whole trip in just minutes with Orbitz. With Orbitz’s guaranteed low fares, there is no need to wait for special sales to find deals.

Cheap Flights From St. Petersburg - Clearwater to Chicago Through Orbitz

You need a vacation but you have a tight budget, and searching for discount St. Petersburg - Clearwater to Chicago flights has become an exercise in frustration. It's time to stop combing through never-ending search engine results, and go straight to Orbitz.

Guaranteed Low Fares for St. Petersburg - Clearwater to Chicago Flights

Whether you are looking for domestic or international flights, Orbitz offers you the lowest price. With our low price guarantee on flights from St. Petersburg - Clearwater to Chicago, you know you are getting the best deal out there.

Frequent Flyer Miles and Points on Your Flights From St. Petersburg - Clearwater to Chicago

Not only will you pay a low fare through Orbitz, but you can also get credit for frequent flyer miles or points. All you have to do is add your frequent flyer number in the appropriate field when you book St. Petersburg - Clearwater to Chicago flights that qualify.

Arrange Flights From St. Petersburg - Clearwater to Chicago Cutting-Edge Mobile Tools

We know you are busy, so with our mobile apps for Android and iOS devices, you can search for flights, book your seats, and make cancellations while standing in line or in a waiting room. You can also find great discounts on hotel rooms and vacation packages that go with your St. Petersburg - Clearwater to Chicago flights.

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.