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

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Cheap Flights from HOU to MDW starting at $91 One Way, $182 Round Trip

Prices starting at $182 for return flights and $91 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, Sep 11 - Mon, Sep 14
HOU
Houston
MDW
Chicago
$182 Roundtrip, found 14 hours ago
$182
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Fri, Sep 11 from Houston to Chicago, returning Mon, Sep 14, priced at $182 found 14 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
$211 nightly
The price is $251 total per night from Sep 1 to Sep 2
$251 total
Sep 1 - Sep 2
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! (1,255 reviews)
"Check in Staff was great and welcoming, we were allowed to check in early. Room was nice and clean."

Reviewed on Aug 10, 2026

Hyatt Regency McCormick Place Chicago
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$154 nightly
The price is $183 total per night from Sep 8 to Sep 9
$183 total
Sep 8 - Sep 9
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 ...
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
$156 nightly
The price is $185 total per night from Aug 30 to Aug 31
$185 total
Aug 30 - Aug 31
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! (2,492 reviews)
"We were in town for a concert and the room was not ready at check in time of 3pm (did not have a room to get ready in) Staff said they would call us when it was ready and they did not call us. Went back up after an hour of waiting in the lobby and they handed over the keys. Was it ready the whole ..."

Reviewed on Aug 10, 2026

Crowne Plaza Chicago West Loop by IHG
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
$109 nightly
The price is $130 total per night from Sep 8 to Sep 9
$130 total
Sep 8 - Sep 9
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! (10,277 reviews)
"What you are really paying for at this hotel is the location. The rooms were clean, beds good, bathroom was good. Excellent elevators. The building is very old, but so is every building in this area of town. Convenient walk to museums, soldier field, pier. Would stay again."

Reviewed on Aug 10, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$143 nightly
The price is $170 total per night from Aug 30 to Aug 31
$170 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,975 reviews)
"We staying at this property and the experience was incredible! The property, the food, the bar, the rooms everything was great!! It’s in a great location super close to the beach. Walking distance to many shops, restaurants and things to do. The staff were always super helpful. I will just say the ..."

Reviewed on Aug 10, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$210 nightly
The price is $247 total per night from Aug 30 to Aug 31
$247 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hilton 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.

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
$53 nightly
The price is $60 total per night from Sep 1 to Sep 2
$60 total
Sep 1 - Sep 2
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! (2,014 reviews)
"I was diverted overnight through Chicago and this was the only place near the airport with accommodation. It was clean but very outdated and the bed lumpy and uncomfortable. I did not have a great night sleep. If you can pay now and start further away."

Reviewed on Aug 10, 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
$116 nightly
The price is $128 total per night from Aug 31 to Sep 1
$128 total
Aug 31 - Sep 1
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 ...
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
$101 nightly
The price is $116 total per night from Sep 1 to Sep 2
$116 total
Sep 1 - Sep 2
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 ...
7.8/10 Good! (3,139 reviews)
"The property is run down. Only 1 of the elevators worked, booked a king bed and got Two doubles"

Reviewed on Aug 10, 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
$117 nightly
The price is $139 total per night from Aug 31 to Sep 1
$139 total
Aug 31 - Sep 1
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. ...
Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$111 nightly
The price is $132 total per night from Aug 30 to Aug 31
$132 total
Aug 30 - Aug 31
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 ...
7.6/10 Good! (2,755 reviews)
"property was decent given it was an older building. pretty much no outlets in the room and tv either worked for 5 minutes or not at all. no on-site parking and the lot across the street charges outrageous rates. staff was nice and helpful when expedia messed up our reservation."

Reviewed on Aug 10, 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
$53 nightly
The price is $60 total per night from Sep 1 to Sep 2
$60 total
Sep 1 - Sep 2
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! (2,014 reviews)
"I was diverted overnight through Chicago and this was the only place near the airport with accommodation. It was clean but very outdated and the bed lumpy and uncomfortable. I did not have a great night sleep. If you can pay now and start further away."

Reviewed on Aug 10, 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
$197 nightly
The price is $264 total per night from Sep 10 to Sep 11
$264 total
Sep 10 - Sep 11
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! (2,988 reviews)
"When we arrived we didn’t get the hotel room which we booked. They gave another room with one bed which was not comfortable as we booked double beds . They switched next day with the room we booked"

Reviewed on Aug 10, 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
$198 nightly
The price is $236 total per night from Sep 7 to Sep 8
$236 total
Sep 7 - Sep 8
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 ...
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
$161 nightly
The price is $191 total per night from Sep 7 to Sep 8
$191 total
Sep 7 - Sep 8
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! (6,015 reviews)
"Pool was very cold, and no hot tub."

Reviewed on Aug 10, 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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