Southwest® flights from Tampa to Chicago (O'Hare) from $78
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Low fares from Tampa to Chicago (O'Hare)
$
Tampa (TPA)to
Chicago (Midway) (MDW)
Depart: 01/27/2026
One-way
Basic
From
$78
Seen: 3 hrs ago
Tampa (TPA)to
Chicago (Midway) (MDW)
Depart: 02/03/2026
One-way
Basic
From
$78
Seen: 3 hrs ago
Tampa (TPA)to
Chicago (Midway) (MDW)
Depart: 01/17/2026
One-way
Basic
From
$79
Seen: 4 hrs ago
Tampa (TPA)to
Chicago (Midway) (MDW)
Depart: 02/25/2026
One-way
Basic
From
$79
Seen: 3 hrs ago
Tampa (TPA)to
Chicago (Midway) (MDW)
Depart: 01/07/2026
One-way
Basic
From
$79
Seen: 5 hrs ago
Tampa (TPA)to
Chicago (Midway) (MDW)
Depart: 01/21/2026
One-way
Basic
From
$79
Seen: 4 hrs ago
Explore flights from Tampa to Chicago (O'Hare)
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Travel tips for your next Southwest flight
How to board the plane earlier on open seating flights departing on or before January 26, 2026:
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
- Purchase EarlyBird Check-In®1 for automatic check-in and a better boarding position.
- Purchase Upgraded Boarding2 to get an A1-A15 boarding position (depending on availability).
- Purchase a Business Select® fare or upgrade to Business Select to get a guaranteed A1-A15 boarding position.
Enjoy movies, sips, and snacks during your flight.
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Make the most of our Rapid Rewards® Program.
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
Flight Details
Departing from:
Tampa International Airport
Arriving at:
O'Hare International Airport
Distance:
1012 miles
Route Information
97† Weekly flights
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Explore Chicago (O'Hare)
A city of neighborhoods such as Chicago offers a nearly endless number of opportunities to get lost in a new culture, cuisine, or curiosity. The Loop, the central downtown area of the city, is a great place to start if you’re a first-time visitor to Chicago. If the weather is agreeable, one of the best ways to explore the Loop is to take an architectural tour along the Chicago River. Experts on the stunning and iconic buildings will bring you up to speed quickly on the most important landmarks along the riverfront.
Branching out into the neighborhoods is the best way to get a feel for the true character of Chicago. Start your adventure on the Chicago Museum Campus, home to the Field Museum, Adler Planetarium, and more. You’ll easily find the Chicago Lakefront Trail while you’re there. Rent a bike and follow it south to a favorite spot great for picnics and photographs known as Promontory Point and beyond. Traveling north will give you easy access to a number of beaches and popular neighborhoods like Lincoln Park, Lakeview, and Edgewater. There’s no telling where your day might go when you start to explore the vibrant sights, sounds, and delicious smells of these historic neighborhoods.
Questions we hear the most
There are 97 weekly flights from Tampa to Chicago (O'Hare) on Southwest Airlines.
To find the lowest fares by day and time to fly Tampa to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
You can rent a car at O'Hare International Airport book yours with your flight.
Yes! Flights from Tampa to Chicago (O'Hare)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
Explore Flights from Other Popular Origins
Popular Flights from Tampa
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
4Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
5Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
6Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
7Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.