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

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Cheap Flights from TPA to MDW starting at $29 One Way, $58 Round Trip

Prices starting at $58 for return flights and $29 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, Sep 5 - Wed, Sep 11
TPA
Tampa
MDW
Chicago
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Sep 5 from Tampa to Chicago, returning Wed, Sep 11, priced at $58 just found
Wed, Aug 21 - Sat, Aug 24
TPA
Tampa
MDW
Chicago
$64 Roundtrip, found 19 hours ago
$64
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Wed, Aug 21 from Tampa to Chicago, returning Sat, Aug 24, priced at $64 found 19 hours ago
Sat, Sep 14 - Fri, Sep 20
TPA
Tampa
MDW
Chicago
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Sep 14 from Tampa to Chicago, returning Fri, Sep 20, priced at $68 found 1 hour ago
Thu, Sep 5 - Sun, Sep 8
TPA
Tampa
MDW
Chicago
$70 Roundtrip, just found
$70
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Sep 5 from Tampa to Chicago, returning Sun, Sep 8, priced at $70 just found
Tue, Sep 17 - Wed, Oct 2
TPA
Tampa
MDW
Chicago
$73 Roundtrip, found 2 days ago
$73
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 17 from Tampa to Chicago, returning Wed, Oct 2, priced at $73 found 2 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
The price is $132 per night from Jul 1 to Jul 2
$132
per night
Jul 1 - Jul 2
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (2,550 reviews)
"Ok"

Reviewed on Jun 10, 2024

Best Western Grant Park Hotel
Hotel Chicago West Loop
Hotel Chicago West Loop
2.5 out of 5
1622 W Jackson Blvd, Chicago, IL
The price is $152 per night from Jun 18 to Jun 19
$152
per night
Jun 18 - Jun 19
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff ...
8/10 Very Good! (1,016 reviews)
"A lovely hotel, with clean and spacious rooms, very good amenities, and a friendly and responsive staff. I was especially appreciative that they let me check in early, after taking an overnight train from Boston. It made that day a much more pleasant one. Location isn't great for downtown attractions, ..."

Reviewed on Jun 9, 2024

Hotel Chicago West Loop
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $167 per night from Jun 16 to Jun 17
$167
per night
Jun 16 - Jun 17
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (6,870 reviews)
"Fine except for bathroom,"

Reviewed on Jun 8, 2024

Congress Plaza Hotel
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

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $166 per night from Jul 11 to Jul 12
$166
per night
Jul 11 - Jul 12
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,962 reviews)
"Valet parking was terrible, very rude the guy, it’s the only bad thing the hotel have."

Reviewed on Jun 10, 2024

River Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $167 per night from Jun 16 to Jun 17
$167
per night
Jun 16 - Jun 17
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (6,870 reviews)
"Fine except for bathroom,"

Reviewed on Jun 8, 2024

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
The price is $191 per night from Jul 1 to Jul 2
$191
per night
Jul 1 - Jul 2
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
8/10 Very Good! (2,381 reviews)
"IT WAS SO GOOD. GOOD BLACKFAST AND HAPPY HOUR. VERY GOOD LOCATION."

Reviewed on Jun 10, 2024

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.

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 $55 per night from Jun 19 to Jun 20
$55
per night
Jun 19 - Jun 20
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 ...
8/10 Very Good! (1,207 reviews)
"It was very convenient to the airport and the facilities were good too."

Reviewed on Jun 10, 2024

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 East Grand Avenue, Bensenville, IL
The price is $85 per night from Jul 9 to Jul 10
$85
per night
Jul 9 - Jul 10
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.4/10 (1,015 reviews)
"Staff was very nice, rooms were clean & breakfast was good!"

Reviewed on Jun 6, 2024

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 $99 per night from Jun 12 to Jun 13
$99
per night
Jun 12 - Jun 13
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 ...
8.2/10 Very Good! (2,010 reviews)
"Aldi is near"

Reviewed on Jun 8, 2024

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

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 $55 per night from Jun 19 to Jun 20
$55
per night
Jun 19 - Jun 20
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 ...
8/10 Very Good! (1,207 reviews)
"It was very convenient to the airport and the facilities were good too."

Reviewed on Jun 10, 2024

Motel 6 Elk Grove Village, IL - O'Hare
Freehand Chicago
Freehand Chicago
4 out of 5
19 East Ohio Street, Chicago, IL
The price is $112 per night from Jul 10 to Jul 11
$112
per night
Jul 10 - Jul 11
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. ...
7.6/10 Good! (1,041 reviews)
"Thank you for arranging roommate at my age."

Reviewed on Jun 8, 2024

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 $121 per night from Jul 1 to Jul 2
$121
per night
Jul 1 - Jul 2
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.4/10 (1,710 reviews)
"Nice place for one night stay"

Reviewed on Jun 10, 2024

Travelodge by Wyndham Downtown 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.

Family Friendly Hotels in Chicago

Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
The price is $165 per night from Jun 30 to Jul 1
$165
per night
Jun 30 - Jul 1
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 breakfast and the ...
8/10 Very Good! (1,246 reviews)
"Hotel staff was nice room was a little noisy."

Reviewed on Jun 10, 2024

Palmer House a Hilton Hotel
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 $203 per night from Jul 1 to Jul 2
$203
per night
Jul 1 - Jul 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! (2,455 reviews)
"Great services.."

Reviewed on Jun 8, 2024

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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 $191 per night from Jul 1 to Jul 2
$191
per night
Jul 1 - Jul 2
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
8/10 Very Good! (2,381 reviews)
"IT WAS SO GOOD. GOOD BLACKFAST AND HAPPY HOUR. VERY GOOD LOCATION."

Reviewed on Jun 10, 2024

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.

Map To Nearby Hotels

TPA to MDW Route Info

Origin Airport
Tampa
Destination Airport
Chicago
Number Of Airlines Serving
2
Distance
998 mi
Shortest Flight Departure Time
5:20PM CDT
Shortest Flight Departure Date
Jun 18
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.

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.