Cheap flights from Tampa to Chicago from $105
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Tampa to Chicago departing on 11/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Wed 12/16
11:54 am-6:37 pm
1 stop7h 43m
Chicago O'Hare Intl
Sun 12/20
8:10 am-7:41 pm
1 stop10h 31m
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Thu 11/12
12:59 pm-5:47 pm
1 stop5h 48m
Chicago Midway
Sun 11/15
6:42 pm-11:54 am
1 stop16h 12m
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Wed 12/2
4:00 pm-9:30 pm
2 stops6h 30m
Chicago Midway
Sat 12/5
10:20 am-7:15 pm
2 stops7h 55m
TampaChicago
TPA Tampa - MDW Chicago Midway
TPAMDW
Tampa
Wed 12/9
4:00 pm-9:25 pm
2 stops6h 25m
Chicago Midway
Wed 12/16
1:15 pm-8:45 pm
2 stops6h 30m
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Fri 11/6
11:11 pm-12:51 pm
2 stops14h 40m
Chicago O'Hare Intl
Fri 11/13
7:50 pm-6:11 pm
1 stop21h 21m
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Fri 11/6
4:26 pm-6:29 pm
Nonstop3h 03m
Chicago O'Hare Intl
Wed 11/11
7:00 am-2:16 pm
1 stop6h 16m
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Fri 11/6
4:26 pm-6:29 pm
Nonstop3h 03m
Chicago O'Hare Intl
Tue 11/10
7:00 am-2:16 pm
1 stop6h 16m
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Sat 11/14
1:36 pm-6:30 pm
1 stop5h 54m
Chicago O'Hare Intl
Mon 11/16
7:55 am-9:50 am
1 stop24h 55m
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Mon 10/26
6:50 am-8:56 am
Nonstop3h 06m
Chicago O'Hare Intl
Wed 10/28
2:40 pm-6:32 pm
Nonstop2h 52m
TampaChicago
TPA Tampa - ORD Chicago O'Hare Intl
TPAORD
Tampa
Mon 10/26
6:50 am-8:56 am
Nonstop3h 06m
Chicago O'Hare Intl
Wed 11/4
7:02 pm-10:42 pm
Nonstop2h 40m
See travel insights to Chicago from
How to get the cheapest flight ticket from Tampa to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Tampa and Chicago?
Prices are currently typical for flights on this route.
Typical prices usually range from $190 to $372.The lowest price recently found on this route was $208.
What is the cheapest month to fly to Chicago?
The month of February is, on average, the cheapest month to fly to Chicago from Tampa, with most prices found around $201. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Tampa to Chicago during January average around $223.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $363. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Tampa to Chicago for around $532.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Tampa to Chicago during this time can be as low as $336. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $431.
What is the cheapest Tampa to Chicago flight route?
Fly from Tampa to Chicago O'Hare Intl for the best Tampa - Chicago flight prices
How far in advance should I book a flight from Tampa to Chicago?
You are more likely to see cheaper flights to Chicago from Tampa when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $301 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Tampa for as low as $245 on momondo.
What cabin class options are available on Tampa to Chicago flights?
There are 4 cabin classes available to choose from on Tampa to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Tampa to Chicago flights?
You could potentially save up to 25% on your flight if you consider stops on a Tampa to Chicago flight.
How have Tampa to Chicago flight prices changed over time?
As of October 2026, prices for Tampa to Chicago flights are approximately 14% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Tampa to Chicago?
Southwest, United Airlines, and Delta are the most popular carriers operating from Tampa to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Tampa according to our data. United Airlines is the first choice among our users, with 33% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Tampa to Chicago on average per day?
As of October 2026, there are 41 flights per day flying from Tampa to Chicago. The most common time of day flights depart is 12:00PM, with 47% of flights taking off in the afternoon.
How many flights depart from Tampa to Chicago on average per week?
As of October 2026, there are 287 flights per week flying from Tampa to Chicago. The most common day of the week flights depart is Thu, with 16% of flights taking off on this day.
When to book flights from Tampa to Chicago
Cheap Tampa to Chicago (TPA to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Tampa to Chicago
Frequently asked questions about flying from Tampa to Chicago
How far is Tampa to Chicago by plane?
Chicago is 1004.3 mi away from Tampa. Flights usually cover this in 2h 40m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Tampa Airport to Chicago?
Prices for flights from Tampa Airport to Chicago were last updated today.
How many operators does momondo search for flights from Tampa Airport to Chicago?
There are 6 operators available for flights from Tampa Airport to Chicago as of October 2026.
How old do you have to be to fly from Tampa Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Tampa Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Tampa to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Tampa to Chicago is Boeing 737-800 (22.21% of total bookings). The next most popular plane models are Boeing 737-900 (13.88%), Boeing 737 MAX 9 (13.33%), and Boeing 737 MAX 8 (12.45%).
What is the most popular airline from Tampa to Chicago?
momondo data reveals that the most frequently booked airline on the route from Tampa to Chicago is United Airlines, representing 31% of all bookings. The subsequent popular airlines are American Airlines at 23%, Southwest at 23%, and Frontier at 21%.
Best airlines flying from Tampa to Chicago
Compare and see reviews for airlines that fly from Tampa to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $58 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $98 | Free Cancellation | Rating 7.8 8,646 reviews | |||
| PriceFrom $146 | Free Cancellation | Rating 7.1 3,048 reviews | |||
| PriceFrom $156 | Free Cancellation | Rating 7.0 12,146 reviews | |||
| PriceFrom $158 | Free Cancellation | Rating 7.9 4,224 reviews | |||
| PriceFrom $180 | Free Cancellation | Rating 7.4 10,319 reviews |
Southwest Flights From Tampa to Chicago
Southwest flies from Tampa to Chicago around 28 times per week, with 4,224 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Tampa to Chicago in the last 72 hours was $158 (round-trip), much lower than the average airfare cost of $326 for Southwest flights on this route.
United Airlines Flights From Tampa to Chicago
Across 10,319 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Tampa to Chicago about 30 times each week, with ticket deals ranging from $180 to $372. Price data is based on momondo searches in the last 72 hours.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Tampa to Chicago?
It is quick and easy to find Tampa to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Tampa to Chicago with flexible booking policies on momondo?
All flight searches from Tampa to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from Tampa to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Tampa.
I’m not ready to book a flight from Tampa to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Tampa are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.