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

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Cheap Flights from HOU to MDW starting at $47 One Way, $115 Round Trip

Prices starting at $115 for return flights and $47 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.

Fri, Jan 16 - Sun, Jan 18
HOU
Houston
MDW
Chicago
$115 Roundtrip, found 6 days ago
$115
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Jan 16 from Houston to Chicago, returning Sun, Jan 18, priced at $115 found 6 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
710 S Seeley Avenue Chicago IL
$87 nightly
The price is $102 total per night from Dec 14 to Dec 15
$102 total
Dec 14 - Dec 15
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions United Center and Chicago ...
9.6/10 Exceptional! (353 reviews)
Room was spacious with a great view. Staff was very friendly.

Reviewed on Dec 3, 2025

Hampton Inn & Suites Chicago Medical District UIC
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
$86 nightly
The price is $100 total per night from Dec 14 to Dec 15
$100 total
Dec 14 - Dec 15
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 ...
8.8/10 Excellent! (1,733 reviews)
Courteous staff Clean room

Reviewed on Dec 2, 2025

Crowne Plaza Chicago West Loop by IHG
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
$79 nightly
The price is $93 total per night from Jan 5 to Jan 6
$93 total
Jan 5 - Jan 6, 2026
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 ...
8.6/10 Excellent! (2,120 reviews)
Great experience with accommodating staff. The room was very clean!

Reviewed on Dec 3, 2025

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

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
$94 nightly
The price is $111 total per night from Dec 18 to Dec 19
$111 total
Dec 18 - Dec 19
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 ...
8.4/10 Very Good! (5,366 reviews)
Very good experience!

Reviewed on Dec 7, 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$105 nightly
The price is $123 total per night from Dec 14 to Dec 15
$123 total
Dec 14 - Dec 15
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (3,435 reviews)
n/a

Reviewed on Dec 6, 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
9.2/10 Wonderful! (2,096 reviews)
Would stay again.

Reviewed on Dec 3, 2025

Silversmith Hotel Chicago Downtown
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
$52 nightly
The price is $59 total per night from Dec 22 to Dec 23
$59 total
Dec 22 - Dec 23
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! (1,713 reviews)
I love this Motel 6, everyone is amazing here!

Reviewed on Dec 5, 2025

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
$95 nightly
The price is $106 total per night from Jan 1 to Jan 2
$106 total
Jan 1 - Jan 2, 2026
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 ...
7.2/10 Good! (1,201 reviews)
The staff was very helpful and professional.

Reviewed on Nov 30, 2025

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
$67 nightly
The price is $77 total per night from Dec 21 to Dec 22
$77 total
Dec 21 - Dec 22
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! (2,748 reviews)
I love the Comfort Inn and frequent this location often, Uno’s pizzeria in the building is also a big plus. The staff is always friendly and helpful. The few times I had breakfast it was tasty, my only complaint would be the let out sofa. Please replace the sofa’s they are very outdated. I sat down ...

Reviewed on Dec 4, 2025

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
The price is $87 total per night from Jan 4 to Jan 5
$87 total
per night
Jan 4 - Jan 5
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. ...
7.8/10 Good! (2,621 reviews)
Great location

Reviewed on Dec 5, 2025

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 $99 total per night from Jan 5 to Jan 6
$99 total
per night
Jan 5 - Jan 6
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 ...
7.2/10 Good! (2,486 reviews)
Good

Reviewed on Dec 6, 2025

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
The price is $59 total per night from Dec 22 to Dec 23
$59 total
per night
Dec 22 - Dec 23
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! (1,713 reviews)
I love this Motel 6, everyone is amazing here!

Reviewed on Dec 5, 2025

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
The price is $128 total per night from Jan 6 to Jan 7
$128 total
per night
Jan 6 - Jan 7
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! (2,740 reviews)
It was great! I would stay there again😊

Reviewed on Dec 5, 2025

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
The price is $145 total per night from Dec 28 to Dec 29
$145 total
per night
Dec 28 - Dec 29
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 ...
8.4/10 Very Good! (2,115 reviews)
great stay

Reviewed on Dec 5, 2025

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
The price is $111 total per night from Dec 18 to Dec 19
$111 total
per night
Dec 18 - Dec 19
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 ...
8.4/10 Very Good! (5,366 reviews)
Very good experience!

Reviewed on Dec 7, 2025

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
HOU Address & GPS
Address:
7800 Airport Boulevard
Houston TX, 77061
United States
IATA Code:
HOU
Longitude:
-95.277018
Latitude:
29.654513
Time Zone:
America/Chicago
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 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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