$59 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, Jun 29 - Thu, Jul 3
TPA
Tampa Intl.
MDW
Midway Intl.
$244 Roundtrip, found 2 hours ago
$244
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Jun 29 from Tampa Intl. to Midway Intl., returning Thu, Jul 3, priced at $244 found 2 hours ago
Sun, Jun 29 - Thu, Jul 3
TPA
Tampa Intl.
ORD
O'Hare Intl.
$281 Roundtrip, found 2 hours ago
$281
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Jun 29 from Tampa Intl. to O'Hare Intl., returning Thu, Jul 3, priced at $281 found 2 hours ago
Sat, Jun 28 - Mon, Jun 30
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$467 Roundtrip, found 3 days ago
$467
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jun 28 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Mon, Jun 30, priced at $467 found 3 days ago
Sat, Jun 28 - Mon, Jun 30
SRQ
Sarasota-Bradenton Intl.
MDW
Midway Intl.
$568 Roundtrip, found 3 days ago
$568
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jun 28 from Sarasota-Bradenton Intl. to Midway Intl., returning Mon, Jun 30, priced at $568 found 3 days ago

Airfares from $59 One Way, $114 Round Trip from St. Petersburg - Clearwater to Chicago

Prices starting at $114 for return flights and $59 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 9 - Tue, Jul 15
TPA
Tampa
ORD
Chicago
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Jul 9 from Tampa to Chicago, returning Tue, Jul 15, priced at $114 just found
Thu, Aug 21 - Mon, Aug 25
TPA
Tampa
ORD
Chicago
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 21 from Tampa to Chicago, returning Mon, Aug 25, priced at $139 found 1 day ago
Fri, Sep 19 - Mon, Sep 22
TPA
Tampa
ORD
Chicago
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Sep 19 from Tampa to Chicago, returning Mon, Sep 22, priced at $197 found 1 hour ago
Thu, Sep 11 - Wed, Sep 17
TPA
Tampa
ORD
Chicago
$217 Roundtrip, found 20 hours ago
$217
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Thu, Sep 11 from Tampa to Chicago, returning Wed, Sep 17, priced at $217 found 20 hours ago
Wed, Oct 8 - Wed, Oct 15
SRQ
Sarasota
ORD
Chicago
$223 Roundtrip, found 2 days ago
$223
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 8 from Sarasota to Chicago, returning Wed, Oct 15, priced at $223 found 2 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
3.5-star property

Congress Plaza Hotel

8/10 Very Good! (8,858 reviews)

Jul 23 - Jul 26

3 night stay

Tampa (TPA) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
It’s was easy- we were in our rooms within a Few minutes of arriving

Reviewed on Jun 1, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,008 reviews)

Jul 23 - Jul 26

3 night stay

Tampa (TPA) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,609 reviews)

Jul 23 - Jul 26

3 night stay

Tampa (TPA) to Chicago (ORD)

Spirit Airlines • 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

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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

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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.