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, $183 Round Trip

Prices starting at $183 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.

Tue, Jun 9 - Tue, Jun 23
HOU
Houston
MDW
Chicago
$183 Roundtrip, found 5 hours ago
$183
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Houston to Chicago, returning Tue, Jun 23, priced at $183 found 5 hours ago
Tue, Jun 9 - Tue, Jun 23
HOU
Houston
MDW
Chicago
$193 Roundtrip, found 5 hours ago
$193
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Houston to Chicago, returning Tue, Jun 23, priced at $193 found 5 hours ago
Tue, Jun 9 - Tue, Jun 23
HOU
Houston
MDW
Chicago
$199 Roundtrip, found 5 hours ago
$199
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Houston to Chicago, returning Tue, Jun 23, priced at $199 found 5 hours ago
Tue, Oct 6 - Sat, Oct 17
HOU
Houston
MDW
Chicago
$199 Roundtrip, found 6 days ago
$199
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Oct 6 from Houston to Chicago, returning Sat, Oct 17, priced at $199 found 6 days ago
Tue, Jun 9 - Tue, Jun 23
HOU
Houston
MDW
Chicago
$203 Roundtrip, found 5 hours ago
$203
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Jun 9 from Houston to Chicago, returning Tue, Jun 23, priced at $203 found 5 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
$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 free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (2,172 reviews)
The staff were very welcoming and friendly. Our room was very clean and quiet. We will definitely be back!

Reviewed on May 14, 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! (10,225 reviews)
The hot water didn’t work while trying to shower and there was hair in the bed upon arrival

Reviewed on May 14, 2026

Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$134 nightly
The price is $160 total per night from May 25 to May 26
$160 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 room service. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,997 reviews)
Recommend.

Reviewed on May 13, 2026

Hilton Garden Inn 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

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! (10,225 reviews)
The hot water didn’t work while trying to shower and there was hair in the bed upon arrival

Reviewed on May 14, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$150 nightly
The price is $179 total per night from May 25 to May 26
$179 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! (4,136 reviews)
The property, our room, and the staff were all FIVE STARS! Highly recommend this place!!

Reviewed on May 13, 2026

Hotel Riu Plaza Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$144 nightly
The price is $171 total per night from May 25 to May 26
$171 total
May 25 - May 26
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! (5,166 reviews)
Friendly staff and excellent location. Loved our 2 bed suite with 2 bathrooms and a kitchen! Would absolutely stay again!

Reviewed on May 11, 2026

River 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.

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 19 to May 20
$68 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! (1,930 reviews)
Was very disappointed that there was no airport shuttle. Not sure where but I read somewhere that there was one and to just call the hotel on arrival. Nope...added $50 to my stay.

Reviewed on May 13, 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 May 25 to May 26
$112 total
May 25 - May 26
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! (1,416 reviews)
Bathroom was really dirty. The hotel looked so dark and shady. Room didn’t had enough light either. Asked front desk that bathroom is not clean, the answer was there is no one available to clean and didn’t offer different room either instead offered extra towels. Will not recommend to anyone or go ...

Reviewed on May 13, 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 25 to May 26
$110 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! (3,026 reviews)
No waffle maker.

Reviewed on May 13, 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! (2,986 reviews)
The room is dated and overpriced for the lack of amenities in the room. Heater was not working during stay. Not properly cleaned with left over hair ties. The breakfast bar and lounge bar are a nice touch, however the staff is rude and not very willing to help. The manager of the hotel being one ...

Reviewed on May 13, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$117 nightly
The price is $139 total per night from May 25 to May 26
$139 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! (2,582 reviews)
Great

Reviewed on May 13, 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 19 to May 20
$68 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! (1,930 reviews)
Was very disappointed that there was no airport shuttle. Not sure where but I read somewhere that there was one and to just call the hotel on arrival. Nope...added $50 to my stay.

Reviewed on May 13, 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
$176 nightly
The price is $209 total per night from May 25 to May 26
$209 total
May 25 - May 26
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! (2,867 reviews)
Excellent breakfast.

Reviewed on May 12, 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
$168 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! (2,445 reviews)
Beautiful hotel , we had a wonderful stay

Reviewed on May 13, 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 25 to May 26
$174 total
May 25 - May 26
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,927 reviews)
Great location$ access to many things

Reviewed on May 13, 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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