Cheap flights from HOU to MDW (William P. Hobby to Midway Intl.)

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Cheap Flights from HOU to MDW starting at $85 One Way, $169 Round Trip

Prices starting at $169 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 22 - Wed, Jul 29
HOU
Houston
MDW
Chicago
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jul 22 from Houston to Chicago, returning Wed, Jul 29, priced at $169 found 5 days ago
Wed, Jul 22 - Wed, Jul 29
HOU
Houston
MDW
Chicago
$175 Roundtrip, found 5 days ago
$175
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jul 22 from Houston to Chicago, returning Wed, Jul 29, priced at $175 found 5 days ago
Wed, Jul 22 - Wed, Jul 29
HOU
Houston
MDW
Chicago
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jul 22 from Houston to Chicago, returning Wed, Jul 29, priced at $179 found 5 days ago
Tue, Jul 28 - Tue, Aug 4
HOU
Houston
MDW
Chicago
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jul 28 from Houston to Chicago, returning Tue, Aug 4, priced at $183 found 5 days ago
Wed, Jul 22 - Wed, Jul 29
HOU
Houston
MDW
Chicago
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jul 22 from Houston to Chicago, returning Wed, Jul 29, priced at $189 found 5 days 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
$224 nightly
The price is $266 total per night from May 22 to May 23
$266 total
May 22 - May 23
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! (1,076 reviews)
"Very quiet and clean and very big gym"

Reviewed on May 14, 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
$145 nightly
The price is $172 total per night from May 25 to May 26
$172 total
May 25 - May 26
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! (2,186 reviews)
"Kitchen was out of service for some unknown reason so could not get dinner or breakfast and the bar closed at 10pm so couldn’t even have a drink when we got back from the theater."

Reviewed on May 19, 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
$135 nightly
The price is $161 total per night from May 25 to May 26
$161 total
May 25 - May 26
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! (10,167 reviews)
"I had an amazing view of Lake Michigan and the area but unfortunately Michigan Ave is very noisy at all times of the day and night. In addition, there were no black out shades and due to the rooms facing East, the sunrise was bright and early. I had to buy a sleeping mask just to sleep to 7am. The ..."

Reviewed on May 19, 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
$135 nightly
The price is $161 total per night from May 25 to May 26
$161 total
May 25 - May 26
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! (10,167 reviews)
"I had an amazing view of Lake Michigan and the area but unfortunately Michigan Ave is very noisy at all times of the day and night. In addition, there were no black out shades and due to the rooms facing East, the sunrise was bright and early. I had to buy a sleeping mask just to sleep to 7am. The ..."

Reviewed on May 19, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$165 nightly
The price is $197 total per night from May 25 to May 26
$197 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 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,193 reviews)
"Our stay at the Hotel Riu was excellent. The staff was very professional and accommodating. The breakfast buffet had a great selection. The rooftop bar was a great atmosphere. We'll definitely return to stay again."

Reviewed on May 20, 2026

Hotel Riu Plaza Chicago
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
$119 nightly
The price is $142 total per night from May 26 to May 27
$142 total
May 26 - May 27
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! (2,706 reviews)
"The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation. Other than that we had a very enjoyable stay. The location is great!"

Reviewed on May 19, 2026

Hotel Felix River North/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 May 25 to May 26
$68 total
May 25 - May 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 ...
7.8/10 Good! (1,924 reviews)
"Yes. Excellent"

Reviewed on May 19, 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
$106 nightly
The price is $117 total per night from May 27 to May 28
$117 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 ...
7.6/10 Good! (1,436 reviews)
"Breakfast was awesome fresh coffee and also the pool was definitely relaxing after working in the kitchen at aggtuccis in Peoria il the shower was really nice to and it was overall the best stay in a hotel I have ever been in thanks again keegan Johnston from Peoria il"

Reviewed on May 19, 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
$96 nightly
The price is $110 total per night from May 26 to May 27
$110 total
May 26 - May 27
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! (3,015 reviews)
"Breakfast was fresh. Charging $20 for parking seemed a bit high. Restaurant was good. Shower never turned off. Workout area was closed"

Reviewed on May 19, 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
$95 nightly
The price is $113 total per night from May 25 to May 26
$113 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! (3,023 reviews)
"The lights in the room didn’t work. The door didn’t close properly. There was about 12” of free space surrounding the bed."

Reviewed on May 20, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$113 nightly
The price is $135 total per night from May 25 to May 26
$135 total
May 25 - May 26
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! (2,597 reviews)
"Old building, but clean and bed was comfortable- restaurants next door great. Very little amenities, not fancy but clean"

Reviewed on May 20, 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
$60 nightly
The price is $68 total per night from May 25 to May 26
$68 total
May 25 - May 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 ...
7.8/10 Good! (1,924 reviews)
"Yes. Excellent"

Reviewed on May 19, 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
$172 nightly
The price is $204 total per night from May 26 to May 27
$204 total
May 26 - May 27
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! (2,858 reviews)
"Best hotel breakfast around...for free! Excellent buffet, and cook to order omelets are restaurant quality"

Reviewed on May 19, 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 May 26 to May 27
$248 total
May 26 - May 27
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! (2,459 reviews)
"This is a grand old hotel. The staff was friendly and very helpful."

Reviewed on May 20, 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
$147 nightly
The price is $174 total per night from May 26 to May 27
$174 total
May 26 - May 27
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! (5,933 reviews)
"Breakfast is so bad-tasting filled with annoying kids"

Reviewed on May 20, 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.

HOU to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date

Frequently asked questions

Are there non-stop flights from HOU to Chicago Airport?
We're about to make your upcoming vacation even more exciting. Southwest Airlines flies nonstop from HOU to Midway Intl. Airport (MDW), so you'll be starting your awesome adventure in no time at all.
What is the shortest flight from William P. Hobby Airport to Chicago Airport?
If the weather is good and all goes according to plan, you could be landing at Midway Intl. Airport (MDW) from HOU in just 2 hours and 20 minutes. With such a brief flight time, consider taking just hand luggage.
How many hours flight from HOU to Chicago Airport?
On average, the flight time from HOU to MDW is just 2 hours and 23 minutes. So, pack your bags and lock in your seat. There's nothing more fun than a spontaneous getaway.
What airlines have the most flights from William P. Hobby Airport (HOU) to Chicago Airport?
Ready to book your Houston to Chicago airfare? Consider making Southwest Airlines your first choice. With 132 flights per month to select from on this route, they've got the ticket to your next exciting adventure.

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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