Cheap flights from TPA to MDW (Tampa Intl. to Midway Intl.)

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Cheap Flights from TPA to MDW starting at $71 One Way, $148 Round Trip

Prices starting at $148 for return flights and $71 for one-way flights to Midway Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Feb 26 - Sat, Feb 28
TPA
Tampa
MDW
Chicago
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Tampa to Chicago, returning Sat, Feb 28, priced at $148 found 2 days ago
Thu, Feb 19 - Mon, Feb 23
TPA
Tampa
MDW
Chicago
$155 Roundtrip, found 2 days ago
$155
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Tampa to Chicago, returning Mon, Feb 23, priced at $155 found 2 days ago
Thu, May 7 - Mon, May 11
TPA
Tampa
MDW
Chicago
$160 Roundtrip, found 16 hours ago
$160
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Thu, May 7 from Tampa to Chicago, returning Mon, May 11, priced at $160 found 16 hours ago
Thu, Feb 19 - Mon, Feb 23
TPA
Tampa
MDW
Chicago
$176 Roundtrip, found 2 days ago
$176
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Tampa to Chicago, returning Mon, Feb 23, priced at $176 found 2 days ago
Mon, May 11 - Tue, May 12
TPA
Tampa
MDW
Chicago
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 11 from Tampa to Chicago, returning Tue, May 12, priced at $181 found 1 day ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$95 nightly
The price is $112 total per night from Feb 4 to Feb 5
$112 total
Feb 4 - Feb 5
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,839 reviews)
Great a+++

Reviewed on Feb 1, 2026

Congress Plaza Hotel
Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 out of 5
105 N MAY STREET Chicago IL
$144 nightly
The price is $169 total per night from Feb 15 to Feb 16
$169 total
Feb 15 - Feb 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.8/10 Excellent! (1,174 reviews)
The room was clean however a lot of noise in the hallway late last night with people talking between 11pm and 2am which kept me awake

Reviewed on Feb 1, 2026

Hyatt House Chicago West Loop
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
$99 nightly
The price is $116 total per night from Feb 8 to Feb 9
$116 total
Feb 8 - Feb 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,941 reviews)
Room was great. However, the lobby had no coffee @ 0800 when we went to get some.

Reviewed on Jan 31, 2026

Crowne Plaza Chicago West Loop by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$95 nightly
The price is $112 total per night from Feb 4 to Feb 5
$112 total
Feb 4 - Feb 5
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,839 reviews)
Great a+++

Reviewed on Feb 1, 2026

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$107 nightly
The price is $125 total per night from Feb 9 to Feb 10
$125 total
Feb 9 - Feb 10
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.4/10 Very Good! (5,638 reviews)
Staff are goid ,clean room,just one comment M

Reviewed on Feb 3, 2026

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$164 nightly
The price is $192 total per night from Feb 21 to Feb 22
$192 total
Feb 21 - Feb 22
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,594 reviews)
Some of the nicest people you'll ever meet! Excellent location for a Bears game stay, walking distance to Soldier Field.

Reviewed on Feb 1, 2026

Hilton Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chicago Hotels With Airport Transportation

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
$38 nightly
The price is $43 total per night from Feb 16 to Feb 17
$43 total
Feb 16 - Feb 17
Total with taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,787 reviews)
Clean room and hot coffee in the morning. Plenty of parking.

Reviewed on Jan 24, 2026

Motel 6 Elk Grove Village, IL - O'Hare
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 E Grand Avenue Bensenville IL
$91 nightly
The price is $101 total per night from Feb 4 to Feb 5
$101 total
Feb 4 - Feb 5
Total with taxes and fees
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.2/10 Good! (1,254 reviews)
Enjoyed my stay

Reviewed on Jan 28, 2026

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
$69 nightly
The price is $79 total per night from Feb 4 to Feb 5
$79 total
Feb 4 - Feb 5
Total with taxes and fees
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8/10 Very Good! (2,852 reviews)
My flight was cancelled and found this hotel in a pinch through Expedia. It was affordable with a shuttle to O’Hare. The property seems pretty old and dated, smells like old carpet. But it had all your basic and essential amenities and a comfortable bed. The staff was nice and the pizza at Uno was ...

Reviewed on Feb 2, 2026

Comfort Suites Chicago O'Hare Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Chicago Hotels

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
$66 nightly
The price is $78 total per night from Feb 9 to Feb 10
$78 total
Feb 9 - Feb 10
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (2,728 reviews)
Super friendly staff. Amazing location, keep it quiet, we do not want this to get out

Reviewed on Jan 28, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$76 nightly
The price is $89 total per night from Feb 4 to Feb 5
$89 total
Feb 4 - Feb 5
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.4/10 Good! (2,512 reviews)
Staff was very courteous and kind. It was only missing a chair in the room. The one thing is that i couldn't find how to keep the heat on.

Reviewed on Jan 31, 2026

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
$38 nightly
The price is $43 total per night from Feb 16 to Feb 17
$43 total
Feb 16 - Feb 17
Total with taxes and fees
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,787 reviews)
Clean room and hot coffee in the morning. Plenty of parking.

Reviewed on Jan 24, 2026

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive Chicago IL
$136 nightly
The price is $160 total per night from Feb 9 to Feb 10
$160 total
Feb 9 - Feb 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,806 reviews)
Room was awesome! Clean and huge! The breakfast was delicious and the cooks were super nice and accomodating. I will be staying at Embassy Suites again. Thank you!

Reviewed on Jan 30, 2026

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
$159 nightly
The price is $183 total per night from Feb 21 to Feb 22
$183 total
Feb 21 - Feb 22
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (2,269 reviews)
Our first stay at Palmer house was a very welcoming experience. The location in downtown Chicago made everything along Michigan ave and surrounding sights easily accessible. The multiple entries were super helpful while walking around and navigating the cold (polar vortex). Ride share and even DoorDash ...

Reviewed on Jan 25, 2026

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
$107 nightly
The price is $125 total per night from Feb 9 to Feb 10
$125 total
Feb 9 - Feb 10
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.4/10 Very Good! (5,638 reviews)
Staff are goid ,clean room,just one comment M

Reviewed on Feb 3, 2026

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

TPA to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
TPA Address & GPS
Address:
5507 West Spruce Street
Tampa FL, 33607
United States
IATA Code:
TPA
Longitude:
-82.535415
Latitude:
27.979869
Time Zone:
America/New_York
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago

Frequently asked questions

Are there non-stop flights from Tampa Airport to Midway Airport?
If you're not a huge fan of layovers, we've got very good news for you. There are multiple air carriers that offer direct flights from Tampa Intl. Airport (TPA) to Midway Intl. Airport (MDW), including Southwest Airlines and Frontier Airlines.
What is the shortest flight from Tampa Intl. Airport (TPA) to Chicago Airport?
It can take as little as 2 hours and 45 minutes to fly from Tampa Airport to Midway Intl. Airport (MDW). Take a seat and enjoy those window views, because you'll be landing before long.
How many hours flight from Tampa Airport to Midway Intl. Airport (MDW)?
There's no reason not to book a Chicago escape when the flight time from TPA to MDW is just 2 hours and 47 minutes on average. Go ahead and grab a ticket — it's about time you finally took a break.
What airlines have the most flights from Tampa Airport to Chicago Airport?
While there are several airlines that have flights from Tampa Airport to Midway Intl. Airport (MDW), there are a couple that stand out in the popularity stakes. Frontier Airlines (F9) is one of the favorites and has 23 flights every month. Southwest Airlines (WN) also flies from Tampa to Chicago. It's another popular choice and has 123 flights each month.

Map To Nearby Hotels

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.

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