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

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Cheap Flights from TPA to MDW starting at $84 One Way, $167 Round Trip

Prices starting at $167 for return flights and $84 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.

Sat, Nov 14 - Tue, Nov 17
TPA
Tampa
MDW
Chicago
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Tampa to Chicago, returning Tue, Nov 17, priced at $167 found 1 day ago
Thu, Dec 3 - Sat, Dec 5
TPA
Tampa
MDW
Chicago
$171 Roundtrip, found 4 hours ago
$171
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Tampa to Chicago, returning Sat, Dec 5, priced at $171 found 4 hours ago
Fri, Dec 11 - Sun, Dec 13
TPA
Tampa
MDW
Chicago
$175 Roundtrip, found 8 hours ago
$175
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, Dec 11 from Tampa to Chicago, returning Sun, Dec 13, priced at $175 found 8 hours ago
Sat, Nov 14 - Wed, Nov 25
TPA
Tampa
MDW
Chicago
$182 Roundtrip, found 21 hours ago
$182
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Tampa to Chicago, returning Wed, Nov 25, priced at $182 found 21 hours ago
Sat, Nov 14 - Sat, Nov 21
TPA
Tampa
MDW
Chicago
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Tampa to Chicago, returning Sat, Nov 21, priced at $183 found 1 day ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$304 nightly
The price is $361 total per night from Oct 23 to Oct 24
$361 total
Oct 23 - Oct 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hyatt Regency McCormick Place Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$108 nightly
The price is $129 total per night from Nov 11 to Nov 12
$129 total
Nov 11 - Nov 12
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! (10,131 reviews)
"This is an old hotel built for the 1893 Worlds fair. But it was cheap and available at the last minute."

Reviewed on Oct 16, 2026

Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$158 nightly
The price is $188 total per night from Nov 11 to Nov 12
$188 total
Nov 11 - Nov 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,248 reviews)
"Beds were nice to come back to after a long day."

Reviewed on Oct 14, 2026

Holiday Inn & Suites Chicago - Downtown 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
$108 nightly
The price is $129 total per night from Nov 11 to Nov 12
$129 total
Nov 11 - Nov 12
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! (10,131 reviews)
"This is an old hotel built for the 1893 Worlds fair. But it was cheap and available at the last minute."

Reviewed on Oct 16, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$152 nightly
The price is $181 total per night from Nov 1 to Nov 2
$181 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,532 reviews)
"Amazing staff very friendly and helpful."

Reviewed on Oct 16, 2026

River Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$142 nightly
The price is $169 total per night from Nov 1 to Nov 2
$169 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
The Chicago Hotel Collection - Magnificent Mile
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
$60 nightly
The price is $68 total per night from Oct 25 to Oct 26
$68 total
Oct 25 - Oct 26
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 ...
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
$100 nightly
The price is $110 total per night from Nov 8 to Nov 9
$110 total
Nov 8 - Nov 9
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 ...
7.6/10 Good! (1,855 reviews)
"We checked in and our room had a musty/ wet dog smell, we found crickets in our room, there were bidets that lined the hallway. We had a pull out sofa, just a sheet no blanket or pillows, asked front desk for them. No extra pillows could be provided they only provide the blanket. The main bed duvet ..."

Reviewed on Oct 16, 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
$97 nightly
The price is $112 total per night from Nov 1 to Nov 2
$112 total
Nov 1 - Nov 2
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 ...
7.8/10 Good! (3,197 reviews)
"Good place to stay for airport layover."

Reviewed on Oct 16, 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
$185 nightly
The price is $220 total per night from Nov 2 to Nov 3
$220 total
Nov 2 - Nov 3
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! (3,394 reviews)
"The room was very clean and the staff was very nice"

Reviewed on Oct 15, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$112 nightly
The price is $133 total per night from Nov 11 to Nov 12
$133 total
Nov 11 - Nov 12
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 ...
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
$60 nightly
The price is $68 total per night from Oct 25 to Oct 26
$68 total
Oct 25 - Oct 26
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 ...
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
$151 nightly
The price is $201 total per night from Nov 1 to Nov 2
$201 total
Nov 1 - Nov 2
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 ...
8.4/10 Very Good! (3,011 reviews)
"This was a nice comfortable stay. It included free breakfast, however, we were not able to get down in time as breakfast ended at 9:30 am and we had a lot of late night plans and preferred to sleep in. The time breakfast ended on the weekend was 10:30am and would’ve been much more convenient if they ..."

Reviewed on Oct 16, 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
$218 nightly
The price is $256 total per night from Oct 31 to Nov 1
$256 total
Oct 31 - Nov 1
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 ...
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
$133 nightly
The price is $181 total per night from Nov 1 to Nov 2
$181 total
Nov 1 - Nov 2
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 ...
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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