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

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Cheap Flights from TPA to MDW starting at $85 One Way, $173 Round Trip

Prices starting at $173 for return flights and $85 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.

Wed, Jul 1 - Wed, Jul 8
TPA
Tampa
MDW
Chicago
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Jul 1 from Tampa to Chicago, returning Wed, Jul 8, priced at $173 found 1 day ago
Tue, Jun 9 - Wed, Jun 10
TPA
Tampa
MDW
Chicago
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jun 9 from Tampa to Chicago, returning Wed, Jun 10, priced at $179 found 2 days ago
Wed, Aug 19 - Wed, Aug 26
TPA
Tampa
MDW
Chicago
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Aug 19 from Tampa to Chicago, returning Wed, Aug 26, priced at $179 found 5 days ago
Wed, Jul 1 - Wed, Jul 8
TPA
Tampa
MDW
Chicago
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Jul 1 from Tampa to Chicago, returning Wed, Jul 8, priced at $183 found 1 day ago
Wed, Jul 1 - Wed, Jul 8
TPA
Tampa
MDW
Chicago
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Jul 1 from Tampa to Chicago, returning Wed, Jul 8, priced at $187 found 1 day 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
$145 nightly
The price is $172 total per night from May 10 to May 11
$172 total
May 10 - May 11
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 ...
9/10 Wonderful! (2,150 reviews)
Friendliest hotel staff ever

Reviewed on May 6, 2026

Crowne Plaza Chicago West Loop by IHG
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$126 nightly
The price is $150 total per night from May 26 to May 27
$150 total
May 26 - May 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,983 reviews)
There was no water at all for sale in their "store." After my room was cleaned, they didn't replenish the water bottles. I went to look for water in their store, and there was none there to purchase at all.

Reviewed on May 5, 2026

Hilton Garden Inn Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
$143 nightly
The price is $170 total per night from May 25 to May 26
$170 total
May 25 - May 26
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! (2,318 reviews)
Good breakfast!

Reviewed on May 5, 2026

Homewood Suites by Hilton Chicago Downtown South Loop
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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
$125 nightly
The price is $148 total per night from May 25 to May 26
$148 total
May 25 - May 26
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,684 reviews)
Friendly staff. Good location

Reviewed on May 5, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$135 nightly
The price is $161 total per night from May 26 to May 27
$161 total
May 26 - May 27
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! (5,172 reviews)
Perfect for couples and the location is amazing

Reviewed on May 6, 2026

River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$151 nightly
The price is $180 total per night from May 27 to May 28
$180 total
May 27 - May 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,072 reviews)
Awesome Breakfast Buffet

Reviewed on May 6, 2026

Hotel Riu Plaza 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
$55 nightly
The price is $62 total per night from May 19 to May 20
$62 total
May 19 - May 20
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! (1,940 reviews)
Staff was friendly. Peaceful and I felt comfortable.

Reviewed on May 6, 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
$100 nightly
The price is $110 total per night from May 27 to May 28
$110 total
May 27 - May 28
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 ...
7.4/10 Good! (1,399 reviews)
Loud construction noise late into night

Reviewed on May 6, 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
$93 nightly
The price is $107 total per night from May 25 to May 26
$107 total
May 25 - May 26
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! (3,005 reviews)
I stayed there 15 years ago and nothing has changed same carpet same bed same everything

Reviewed on May 6, 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
$85 nightly
The price is $101 total per night from May 25 to May 26
$101 total
May 25 - May 26
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. ...
8/10 Very Good! (2,955 reviews)
Best hostel experience ever! I was hesitant of staying in a hostel after not doing so in years but this was so nice and very centrally located. Would stay here again!

Reviewed on May 6, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$106 nightly
The price is $126 total per night from May 10 to May 11
$126 total
May 10 - May 11
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! (2,580 reviews)
Staff very nice Room very clean

Reviewed on May 6, 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
$55 nightly
The price is $62 total per night from May 19 to May 20
$62 total
May 19 - May 20
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! (1,940 reviews)
Staff was friendly. Peaceful and I felt comfortable.

Reviewed on May 6, 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
$180 nightly
The price is $214 total per night from May 10 to May 11
$214 total
May 10 - May 11
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! (2,847 reviews)
Breakfast is the best thing of this place....rooms are old and out-dated. Closet space is terrible, TV and channels are terrible. Bathrooms have no shelves. Great place but could use renovation Staff is friendly.....WiFi is mediocre at best

Reviewed on May 5, 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
$172 nightly
The price is $199 total per night from May 25 to May 26
$199 total
May 25 - May 26
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 ...
8.6/10 Excellent! (2,429 reviews)
Beautiful hotel, staff friendly. Expensive

Reviewed on May 4, 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
$152 nightly
The price is $181 total per night from May 25 to May 26
$181 total
May 25 - May 26
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 ...
8.6/10 Excellent! (5,930 reviews)
Yes

Reviewed on May 5, 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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