Cheap Flight Tickets from Tampa (TPA) to Chicago (MDW), Starting at $221

Good to Know: Cheapest and Fastest TPA - MDW Flights

Useful information for finding best airline tickets from Tampa International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$256

F9 Frontier Airlines • 2 stops • 10h 46m

Oct 14 – Oct 29

The cheapest round trip flight from Tampa to Chicago (TPA-MDW-TPA) is currently $256

🔍 Search Flights

Cheapest One way Flight

$251

WN Southwest Airlines • 1 stop • 17h 10m

Oct 09

The cheapest one way flight from Tampa to Chicago (TPA-MDW) is currently $251

🔍 Search Flights

Cheapest Direct Flight

$221

AA American Airlines • nonstop • 5h 8m

Oct 14

The cheapest nonstop flight from Tampa to Chicago (TPA-MDW) is currently $221

🔍 Search Flights

Fastest Flight

4h

The fastest nonstop flight from Tampa to Chicago (TPA-MDW) takes 4h

Top Airlines Flying from Tampa to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Alaska Airlines -AS

Alaska Airlines

Latest Flight Deals from Tampa (TPA) to Chicago (MDW)

Compare and book low fare round-trip air tickets from Tampa to Chicago. Ideal for travelers with confirmed return itineraries.

Oct 14 - Oct 29, Economy
F9
Tampa → Chicago
10h 46m
5:57 PM - 12:17 PM • 2 stops
F9
Tampa → Chicago
16h 46m
6:16 AM - 6:56 PM • 2 stops
$256
Frontier Airlines
Oct 14 - Oct 29, Economy
UA
Tampa → Chicago
5h 6m
7:26 AM - 9:32 AM • nonstop
UA
Tampa → Chicago
4h 11m
1:55 PM - 5:46 PM • nonstop
$276
United Airlines
Oct 14 - Oct 29, Economy
B6
Tampa → Chicago
33h 54m
3:50 PM - 11:24 AM • 1 stop
B6
Tampa → Chicago
20h 20m
7:00 AM - 8:20 PM • 1 stop
$294
JetBlue Airways
Oct 14 - Oct 29, Economy
WN
Tampa → Chicago
8h 25m
10:35 AM - 2:40 PM • 1 stop
WN
Tampa → Chicago
20h 35m
8:30 AM - 10:05 PM • 1 stop
$432
Southwest Airlines
Oct 14 - Oct 29, Economy
WN
Tampa → Chicago
4h
7:20 AM - 9:00 AM • nonstop
WN
Tampa → Chicago
7h 30m
1:20 PM - 7:10 PM • 1 stop
$438
Southwest Airlines
Oct 14 - Oct 29, Economy
WN
Tampa → Chicago
6h 40m
11:20 AM - 2:20 PM • nonstop
WN
Tampa → Chicago
5h 55m
7:05 AM - 12:00 PM • nonstop
$445
Southwest Airlines

Fly from Tampa to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Tampa to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Tampa to Chicago Flights

What are the airports in Tampa?
TPA
What’s the most popular airline flying from TPA to MDW?
The most popular airline flying from Tampa to Chicago are
Can I fly from TPA to MDW non-stop?
Yes, you can fly TPA to MDW non-stop on
Which airlines fly nonstop between Tampa and Chicago?
The non-stop flights between Tampa and Chicago are .
What’s the earliest departure time from TPA to MDW Airport?
The earliest flight leaves TPA at 7:20 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my Tampa to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from TPA to MDW?
Read the fare rules of the Tampa to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Tampa and Chicago?
operate flights between Tampa and Chicago
How long does a flight from Tampa to Chicago take?
It takes approximately 3 hour to fly non-stop from TPA to MDW, which is 996.59 miles by air.
Which airlines provide the cheapest flights from Tampa (TPA) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from TPA were found on WN : USD 297
Do I need a passport to fly between TPA and MDW?
No
What’s the latest departure time from TPA to MDW ?
The last flight leaves TPA at 9:45 pm

Hotels in Chicago (MDW)

5 hotels near Chicago Midway International — compare rates from top booking sites.

View All Hotels →
4.0-star hotel 4-star hotel

Doubletree By Hilton Hotel Chicago Alsip

📍 5000 West 127th Street, Alsip, Illinois 60803

Compare booking sites Search Deals →
4.0-star hotel 4-star hotel

Hyatt Regency McCormick Place

📍 2233 S Martin Luther King Dr, Chicago, Illinois 60616

Compare booking sites Search Deals →
4.0-star hotel 4-star hotel

MileNorth Hotel

📍 166 E Superior Street, Chicago, Illinois 60611

Compare booking sites Search Deals →
4.0-star hotel 4-star hotel

Sheraton Grand Chicago

📍 301 E North Water St, Chicago, Illinois 60611

Compare booking sites Search Deals →
4.0-star hotel 4-star hotel

The Westin Michigan Avenue Chicago

📍 909 North Michigan Ave, Chicago, Illinois 60611

Compare booking sites Search Deals →
Hotel Deals in Chicago (IL)
Baymont by Wyndham Glenview
Wyndham Hotels & Resorts

Baymont by Wyndham Glenview

8.1/10
★★★☆☆ Hotel 95.0 rooms
✓ Free WiFi ✓ Breakfast

📍 1625 Milwaukee Ave, Chicago (IL), Illinois

At Baymont by Wyndham Glenview, exceptional service and top-notch amenities create a memorable experience for guests.Complimentary internet access is available in the hotel to ensure you stay connect…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$69/night
View Deal
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
Red Roof Inn

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

6.6/10
★★☆☆☆ Hotel 132.0 rooms
✓ Free WiFi

📍 22 West Algonquin Road, Chicago (IL)

Experience an abundance of unparalleled facilities and features at Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts. Maintain seamless communication using the complimentary Wi-Fi at hotel.For visit…

Check-in 03:00 PM  ·  Check-out 12:00 PM

$71/night
View Deal
Radisson Hotel Schaumburg
Choice Hotels

Radisson Hotel Schaumburg

7.0/10
★★★☆☆ Hotel 127.0 rooms
✓ Free WiFi ✓ Breakfast

📍 1550 N. Roselle Rd, Chicago (IL), Illinois

Radisson Hotel Schaumburg provides flawless service and all the necessary facilities for visitors. Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. W…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$91/night
View Deal
WoodSpring Suites Chicago Midway
No chain

WoodSpring Suites Chicago Midway

7.4/10
★★★☆☆ Hotel
✓ Free WiFi

📍 5001 W 79th Street, Chicago (IL)

Check-in 03:00 PM  ·  Check-out 12:00 PM

$100/night
View Deal
La Quinta by Wyndham Chicago O'Hare Airport
Wyndham Hotels & Resorts

La Quinta by Wyndham Chicago O'Hare Airport

8.3/10
★★★☆☆ Hotel 123.0 rooms
✓ Breakfast

📍 6860 Mannheim Rd, Chicago (IL), Illinois

La Quinta by Wyndham Chicago O'Hare Airport offers top-notch services and amenities, ensuring guests experience utmost comfort.Visitors can take advantage of the accessible parking options directly a…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$128/night
View Deal
Quality Inn O'Hare Airport
Choice Hotels

Quality Inn O'Hare Airport

7.6/10
★★★☆☆ Hotel 144.0 rooms
✓ Free WiFi ✓ Breakfast

📍 3801 North Mannheim Road, Chicago (IL), Illinois

Quality Inn O'Hare Airport provides flawless service and all the necessary facilities for visitors.Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. T…

Check-in 02:00 PM  ·  Check-out 11:30 AM

$129/night
View Deal
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
InterContinental Hotels Group

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

8.3/10
★★★★☆ Hotel 503.0 rooms
✓ Free WiFi ✓ Breakfast

📍 5440 North River Road, Chicago (IL), Illinois

Experience an abundance of unparalleled facilities and features at Crowne Plaza Chicago O'Hare Hotel & Conference Center By IHG.Share your photos and respond to emails at your convenience, thanks to …

Check-in 03:00 PM  ·  Check-out 12:00 PM

$159/night
View Deal
Hyatt Regency Schaumburg Chicago
Hyatt Hotels

Hyatt Regency Schaumburg Chicago

8.1/10
★★★★☆ Hotel

📍 1800 E Golf Rd, Chicago (IL)

Great care is taken to ensure guests experience comfort through top-notch services and amenities.Discovering Chicago (IL) becomes even more accessible, thanks to the car hire amenities provided at th…

Check-in 04:00 PM  ·  Check-out 11:00 AM

$161/night
View Deal
Holiday Inn O'Hare Area By IHG
InterContinental Hotels Group

Holiday Inn O'Hare Area By IHG

7.9/10
★★★☆☆ Hotel 245.0 rooms
✓ Free WiFi ✓ Breakfast

📍 5615 North Cumberland Avenue, Chicago (IL), Illinois

Holiday Inn O'Hare Area By IHG offers top-notch services and amenities, ensuring guests experience utmost comfort. Share your photos and respond to emails at your convenience, thanks to the free Wi-F…

Check-in 03:00 PM  ·  Check-out 12:00 PM

$199/night
View Deal

Tampa (TPA) to Chicago (MDW): Airport Information

Origin Airport Tampa International , Tampa, US
Destination Airport Chicago Midway International , Chicago, US
Distance 997 miles

More Flight Options for Tampa (TPA) and Chicago (MDW)

Why Fareleaders for TPA to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Tampa to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on TPA to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Tampa to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Tampa (TPA) to Chicago (MDW)
Terms and Conditions*