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

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Cheap Flights from TPA to MDW starting at $50 One Way, $100 Round Trip

Prices starting at $100 for return flights and $50 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, May 22 - Sun, May 25
TPA
Tampa
MDW
Chicago
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, May 22 from Tampa to Chicago, returning Sun, May 25, priced at $100 just found
Thu, May 22 - Wed, May 28
TPA
Tampa
MDW
Chicago
$129 Roundtrip, found 2 days ago
$129
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, May 22 from Tampa to Chicago, returning Wed, May 28, priced at $129 found 2 days ago
Thu, May 22 - Thu, May 29
TPA
Tampa
MDW
Chicago
$132 Roundtrip, found 3 hours ago
$132
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, May 22 from Tampa to Chicago, returning Thu, May 29, priced at $132 found 3 hours ago
Sun, May 25 - Thu, May 29
TPA
Tampa
MDW
Chicago
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 25 from Tampa to Chicago, returning Thu, May 29, priced at $132 found 1 day ago
Sun, May 25 - Sun, Jun 1
TPA
Tampa
MDW
Chicago
$133 Roundtrip, found 4 hours ago
$133
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, May 25 from Tampa to Chicago, returning Sun, Jun 1, priced at $133 found 4 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

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
The price is $148 per night from May 4 to May 5
$148
includes taxes & fees
$126 per night
May 4 - May 5
Stay at this 3.5-star 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! (1,004 reviews)
"Close to Whole Foods grocery. I didn’t like our room which was the last corner room to the freeway noise."

Reviewed on Apr 22, 2025

Crowne Plaza Chicago West Loop by IHG
Sonder South Wabash
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
The price is $139 per night from Apr 30 to May 1
$139
includes taxes & fees
$118 per night
Apr 30 - May 1
Stay at this 3.5-star aparthotel in Chicago. Enjoy a fitness center, concierge services, and in-room washers/dryers. Popular attractions Soldier Field and Grant ...
8.8/10 Excellent! (481 reviews)
Enjoyable stay
"Decent studio apartment with a well stocked kitchen. Secure building, easy access with codes. Walkable to train and soldier field. Comfy bed, decent sized bathroom. Some noise in hall (doors, people talking) as expected but otherwise fairly quite building. We could hear the train but it didn’t disrupt ..."

Reviewed on Apr 24, 2025

Sonder South Wabash
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
The price is $149 per night from May 26 to May 27
$149
includes taxes & fees
$127 per night
May 26 - May 27
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8/10 Very Good! (1,000 reviews)
"We had a great time on this hotel!!"

Reviewed on Apr 21, 2025

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

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
The price is $175 per night from Apr 30 to May 1
$175
includes taxes & fees
$149 per night
Apr 30 - May 1
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,930 reviews)
"the Location was great"

Reviewed on Apr 23, 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is $235 per night from May 2 to May 3
$235
includes taxes & fees
$200 per night
May 2 - May 3
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
8.8/10 Excellent! (2,074 reviews)
"Clean rooms, great location, next to everything in the city."

Reviewed on Apr 23, 2025

Swissotel - Chicago
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $189 per night from Apr 30 to May 1
$189
includes taxes & fees
$161 per night
Apr 30 - May 1
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,147 reviews)
"Great stay. The only thing is that it said there would be a city view and the view was of the building roofs. Also the pool was closed. The room was lovely and spacious."

Reviewed on Apr 23, 2025

Hilton Chicago/Magnificent Mile Suites
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
The price is $53 per night from Apr 27 to Apr 28
$53
includes taxes & fees
$47 per night
Apr 27 - Apr 28
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! (1,425 reviews)
"Cheap and convenient"

Reviewed on Apr 23, 2025

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
The price is $99 per night from May 26 to May 27
$99
includes taxes & fees
$89 per night
May 26 - May 27
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
6.8/10 (1,005 reviews)
"I never had a chance to book it here"

Reviewed on Apr 22, 2025

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
The price is $102 per night from Apr 27 to Apr 28
$102
includes taxes & fees
$89 per night
Apr 27 - Apr 28
Stay at this 3-star 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! (2,445 reviews)
"Staff very kindly shuttle bus service very fast easy to get to city train station 4minute from hotel lady driver very kind drop us and told details how to get there request for pickup just very fast and easy"

Reviewed on Apr 22, 2025

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
The price is $117 per night from May 26 to May 27
$117
includes taxes & fees
$100 per night
May 26 - May 27
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (1,742 reviews)
"The property is located in the heart of the city of Chicago to serve clients in need of hotel stay, and it maintains high standards of its name. I wish the hotel include breakfast in its services for the clients."

Reviewed on Apr 23, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
The price is $95 per night from Apr 30 to May 1
$95
includes taxes & fees
$81 per night
Apr 30 - May 1
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 ...
6.8/10 (2,106 reviews)
"First time in Chicago and this hotel was in the PERFECT location. Located by so many east transit options, Chicago landmarks and easy dinning/ stores for convenience. The hotel staff was friendly and knowledgeable about the area and easily accessible for any needs. This will be my go to for any Chicago ..."

Reviewed on Apr 23, 2025

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
The price is $53 per night from Apr 27 to Apr 28
$53
includes taxes & fees
$47 per night
Apr 27 - Apr 28
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! (1,425 reviews)
"Cheap and convenient"

Reviewed on Apr 23, 2025

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
The price is $200 per night from May 1 to May 2
$200
includes taxes & fees
$170 per night
May 1 - May 2
Stay at this 4-star 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! (2,653 reviews)
"Our stay was good"

Reviewed on Apr 20, 2025

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
The price is $199 per night from May 26 to May 27
$199
includes taxes & fees
$173 per night
May 26 - May 27
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,693 reviews)
"Socializing with a glass of wine in the bar areas was a high priced luxury! Pool was wonderful, room was comfortable and staff were outstanding."

Reviewed on Apr 23, 2025

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
The price is $175 per night from Apr 30 to May 1
$175
includes taxes & fees
$149 per night
Apr 30 - May 1
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,930 reviews)
"the Location was great"

Reviewed on Apr 23, 2025

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

Am I able to catch a flight from Tampa, FL Airport (TPA-Tampa Intl.) to Chicago, IL Airport (MDW-Midway Intl.) now?
The Covid-19 Travel Advisor can help you with queries about travel restrictions and quarantine when traveling by plane from Tampa, FL Airport (TPA-Tampa Intl.) to Chicago, IL Airport (MDW-Midway Intl.).
Are there non-stop flights from TPA to MDW?
Whether you’re jetting off on a big world adventure or traveling for business purposes, a nonstop flight is the best way to go. With Southwest Airlines you can fly from Tampa Airport to MDW in one easy trip.
What is the shortest flight from Tampa Intl. Airport (TPA) to Chicago Airport?
Flying is one of life’s great pleasures and privileges, especially when your journey is a short and sweet 2 hours and 35 minutes. That’s all it’ll take to make your way from Ozona to West Lawn.
How many hours flight from TPA to MDW?
Don’t get too relaxed in your seat — the general flight time from TPA to Midway Intl. Airport (MDW) is a short 2 hours and 37 minutes.
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago, IL Airport (MDW-Midway Intl.)?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago, IL Airport (MDW-Midway Intl.) have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago, IL Airport (MDW-Midway Intl.) with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago, IL Airport (MDW-Midway Intl.) without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What airlines have the most flights from Tampa Intl. Airport (TPA) to Chicago Airport?
Southwest Airlines is your ticket to an unforgettable vacation. This renowned airline advertises 145 flights each month between Tampa Airport and MDW.

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.