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

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Cheap Flights from TPA to MDW starting at $105 One Way, $209 Round Trip

Prices starting at $209 for return flights and $105 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.

Tue, Jul 28 - Wed, Jul 29
TPA
Tampa
MDW
Chicago
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jul 28 from Tampa to Chicago, returning Wed, Jul 29, priced at $209 found 1 day ago
Tue, Jul 28 - Wed, Jul 29
TPA
Tampa
MDW
Chicago
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jul 28 from Tampa to Chicago, returning Wed, Jul 29, priced at $219 found 1 day ago
Tue, Jun 30 - Tue, Jul 7
TPA
Tampa
MDW
Chicago
$224 Roundtrip, found 13 hours ago
$224
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Tue, Jun 30 from Tampa to Chicago, returning Tue, Jul 7, priced at $224 found 13 hours ago
Tue, Oct 20 - Wed, Oct 21
TPA
Tampa
MDW
Chicago
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Oct 20 from Tampa to Chicago, returning Wed, Oct 21, priced at $225 found 4 days ago
Wed, Sep 23 - Mon, Sep 28
TPA
Tampa
MDW
Chicago
$227 Roundtrip, found 7 hours ago
$227
Roundtrip
found 7 hours ago
Select Southwest Airlines flight, departing Wed, Sep 23 from Tampa to Chicago, returning Mon, Sep 28, priced at $227 found 7 hours 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
$203 nightly
The price is $241 total per night from Jul 2 to Jul 3
$241 total
Jul 2 - Jul 3
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 ...
9.2/10 Wonderful! (1,095 reviews)
"Still-attractive hotel despite being the older of the two hotels next to McCormick Place with excellent beds, adequate space, good facilities. It is a very good choice next to the convention centre given its location and cleanliness. The staff were very helpful."

Reviewed on Jun 2, 2026

Hyatt Regency McCormick Place Chicago
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
$153 nightly
The price is $182 total per night from Jul 6 to Jul 7
$182 total
Jul 6 - Jul 7
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! (2,239 reviews)
"I had an amazing time in Chicago, not one complaint. Everyone was pleasant and my room was clean."

Reviewed on Jun 4, 2026

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$145 nightly
The price is $173 total per night from Jun 29 to Jun 30
$173 total
Jun 29 - Jun 30
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! (10,175 reviews)
"We had a clean room, the staff was attentive. It was a great experience!"

Reviewed on Jun 5, 2026

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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$145 nightly
The price is $173 total per night from Jun 29 to Jun 30
$173 total
Jun 29 - Jun 30
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! (10,175 reviews)
"We had a clean room, the staff was attentive. It was a great experience!"

Reviewed on Jun 5, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$154 nightly
The price is $183 total per night from Jun 28 to Jun 29
$183 total
Jun 28 - Jun 29
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 ...
7.8/10 Good! (1,520 reviews)
"👍"

Reviewed on Jun 5, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,619 reviews)
"Very helpful, polite and nice staff. Clean and confortable rooms. Close to airport."

Reviewed on Jun 5, 2026

Hyatt Regency O'Hare 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
$65 nightly
The price is $73 total per night from Jun 29 to Jun 30
$73 total
Jun 29 - Jun 30
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! (1,949 reviews)
"For a simple stay, this place fits the bill. The staff was awesome. The area doesn’t have much but a Subway Sandwich shop that’s open til 11pm on Sundays, which was a plus for me, so plan on renting a car or grabbing a ride share for all of your activities."

Reviewed on Jun 3, 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
$101 nightly
The price is $112 total per night from Jun 29 to Jun 30
$112 total
Jun 29 - Jun 30
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! (1,480 reviews)
"Staff were kind but the room was disgusting. I am not exaggerating when I say I peeled back the sheets are there was tons of hair everywhere. Almost as if cleaning staff just remade a dirty bed. The shower also had TONS of hair in it. Floor had big debris all over it so no one clearly swept. Imagine ..."

Reviewed on Jun 5, 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
$94 nightly
The price is $108 total per night from Jun 8 to Jun 9
$108 total
Jun 8 - Jun 9
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! (3,032 reviews)
"The bus shuttle operator was rude and wasn't accurate i was taken Schaumburg when I wanted to go to Schiller park"

Reviewed on Jun 4, 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
$137 nightly
The price is $162 total per night from Jul 6 to Jul 7
$162 total
Jul 6 - Jul 7
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! (3,063 reviews)
"If you’re looking for a bare bones place to stay, that’s very reasonable. If you don’t need a television in your room or amenities in the bathroom. It is a great place to just lay your head and sleep while you spend the rest of your time out in the city."

Reviewed on Jun 5, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$134 nightly
The price is $159 total per night from Jun 28 to Jun 29
$159 total
Jun 28 - Jun 29
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! (2,601 reviews)
"Great walking location to Grant Park & Millennium Park. Also close to bus stops"

Reviewed on Jun 5, 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
$65 nightly
The price is $73 total per night from Jun 29 to Jun 30
$73 total
Jun 29 - Jun 30
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! (1,949 reviews)
"For a simple stay, this place fits the bill. The staff was awesome. The area doesn’t have much but a Subway Sandwich shop that’s open til 11pm on Sundays, which was a plus for me, so plan on renting a car or grabbing a ride share for all of your activities."

Reviewed on Jun 3, 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
$239 nightly
The price is $284 total per night from Jul 6 to Jul 7
$284 total
Jul 6 - Jul 7
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! (2,870 reviews)
"Over all it was a pleasant stay. My only complaint was I reported the Kerig wasn't working and they said they would replace it however they never did. There were not many options on their menu for us who have celiac. The woman taking omlet orders was very kind and they were delicious and amazingly ..."

Reviewed on Jun 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
$209 nightly
The price is $248 total per night from Jul 2 to Jul 3
$248 total
Jul 2 - Jul 3
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! (2,476 reviews)
"Check in was horrible. The longest lines you can imagine….face me 250 Hilton points….not useful for me. Property is beautiful if you look closely but it is not well maintained."

Reviewed on Jun 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
$208 nightly
The price is $247 total per night from Jun 14 to Jun 15
$247 total
Jun 14 - Jun 15
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! (5,959 reviews)
"staff was very professional"

Reviewed on Jun 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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