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

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Cheap Flights from HOU to MDW starting at $96 One Way, $187 Round Trip

Prices starting at $187 for return flights and $96 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, Apr 28 - Wed, Apr 29
HOU
Houston
MDW
Chicago
$187 Roundtrip, found 6 days ago
$187
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Apr 28 from Houston to Chicago, returning Wed, Apr 29, priced at $187 found 6 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$124 nightly
The price is $146 total per night from Apr 5 to Apr 6
$146 total
Apr 5 - Apr 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,009 reviews)
The room was clean with no issues. Very limited parking on site, but there is a parking lot adjacent to the property that isn't associated with the hotel.

Reviewed on Mar 29, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
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
$131 nightly
The price is $154 total per night from Apr 27 to Apr 28
$154 total
Apr 27 - Apr 28
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! (2,041 reviews)
Out of coffee at 8 in the morning

Reviewed on Mar 29, 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
$110 nightly
The price is $129 total per night from Apr 5 to Apr 6
$129 total
Apr 5 - Apr 6
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! (1,939 reviews)
No room service, there 3 nights, the didn’t show up until the final day when they entered room without knocking almost 2 hours before checkout : I was naked

Reviewed on Mar 29, 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
$115 nightly
The price is $135 total per night from Apr 5 to Apr 6
$135 total
Apr 5 - Apr 6
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! (10,014 reviews)
N/A

Reviewed on Mar 30, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$122 nightly
The price is $143 total per night from Apr 6 to Apr 7
$143 total
Apr 6 - Apr 7
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 ...
9/10 Wonderful! (4,020 reviews)
Great location and great service

Reviewed on Mar 30, 2026

Hilton Chicago/Magnificent Mile Suites
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
$127 nightly
The price is $149 total per night from Apr 12 to Apr 13
$149 total
Apr 12 - Apr 13
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! (5,800 reviews)
Our stay was ok. It was very crowded and we could hear the family in the room next door. Because it was crowded, you had to wait for elevators for a while. Or ride on completely packed elevators. Especially in the morning during breakfast hours. Water pressure is extremely weak in the shower. Room ...

Reviewed on Mar 30, 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.

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 Apr 21 to Apr 22
$62 total
Apr 21 - Apr 22
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! (1,895 reviews)
Yes

Reviewed on Mar 29, 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
$95 nightly
The price is $106 total per night from Apr 19 to Apr 20
$106 total
Apr 19 - Apr 20
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! (1,326 reviews)
Parking for the stay and park option should be parking only in the upper lot. There were 2 handicapp parking spots both were being used by people gone for 4 or more days. Maintenance should put chemicals in and refill hot tub/pool at night so patrons can use it during open hours. Hotel staff were ...

Reviewed on Mar 30, 2026

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
O'Hare Inn & Suites

O'Hare Inn & Suites

2 out of 5
4101 Mannheim Rd Schiller Park IL
$64 nightly
The price is $72 total per night from Apr 1 to Apr 2
$72 total
Apr 1 - Apr 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Allstate Arena and Fashion ...
5.8/10 (1,006 reviews)
Walls are thin. Can hear everything in hall, rooms next to you and outside. Very challenging to sleep before a flight

Reviewed on Mar 21, 2026

O'Hare Inn & Suites
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
$79 nightly
The price is $93 total per night from Apr 14 to Apr 15
$93 total
Apr 14 - Apr 15
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! (2,836 reviews)
Fantastic staff; very helpful when I had a problem. The elevator was having issues, and I had an unfortunate roommate (watching horror movies all night but hiding when security showed up) but the bed linens were great and the room smelled clean. The shower kinda leaked all over the bathroom, which ...

Reviewed on Mar 30, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$103 nightly
The price is $121 total per night from Mar 31 to Apr 1
$121 total
Mar 31 - Apr 1
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! (2,537 reviews)
This was our third year in a row staying at this same hotel. It has very convenient parking, walkability to pretty much everything and the rooms are big and spacious. We will always stay here when we visit Chicago!

Reviewed on Mar 29, 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 Apr 21 to Apr 22
$62 total
Apr 21 - Apr 22
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! (1,895 reviews)
Yes

Reviewed on Mar 29, 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
$144 nightly
The price is $169 total per night from Apr 6 to Apr 7
$169 total
Apr 6 - Apr 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! (2,821 reviews)
Everything was great except they only had 2 of 4 elevators operating and the waits for an elevator were very long

Reviewed on Mar 30, 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
$159 nightly
The price is $183 total per night from Apr 5 to Apr 6
$183 total
Apr 5 - Apr 6
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! (2,342 reviews)
Our room was very comfortable. The beds and pillows were very nice

Reviewed on Mar 29, 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
$127 nightly
The price is $149 total per night from Apr 12 to Apr 13
$149 total
Apr 12 - Apr 13
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! (5,800 reviews)
Our stay was ok. It was very crowded and we could hear the family in the room next door. Because it was crowded, you had to wait for elevators for a while. Or ride on completely packed elevators. Especially in the morning during breakfast hours. Water pressure is extremely weak in the shower. Room ...

Reviewed on Mar 30, 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
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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