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, $94 Round Trip

Prices starting at $94 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.

Thu, Aug 14 - Mon, Aug 18
HOU
Houston
MDW
Chicago
$94 Roundtrip, found 2 days ago
$94
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Aug 14 from Houston to Chicago, returning Mon, Aug 18, priced at $94 found 2 days ago
Thu, Oct 2 - Mon, Oct 6
IAH
Houston
MDW
Chicago
$104 Roundtrip, found 3 days ago
$104
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Oct 2 from Houston to Chicago, returning Mon, Oct 6, priced at $104 found 3 days ago
Thu, Sep 4 - Mon, Sep 8
IAH
Houston
MDW
Chicago
$106 Roundtrip, found 3 days ago
$106
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Houston to Chicago, returning Mon, Sep 8, priced at $106 found 3 days ago
Fri, Aug 22 - Mon, Aug 25
HOU
Houston
MDW
Chicago
$106 Roundtrip, found 1 day ago
$106
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Aug 22 from Houston to Chicago, returning Mon, Aug 25, priced at $106 found 1 day ago
Fri, Aug 15 - Tue, Aug 19
HOU
Houston
MDW
Chicago
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Aug 15 from Houston to Chicago, returning Tue, Aug 19, priced at $108 found 3 days 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
$147 nightly
The price is $173 total per night from Aug 10 to Aug 11
$173 total
Aug 10 - Aug 11
Total includes taxes and fees
Stay at this 3.5-star 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! (1,238 reviews)
"Great location and hotel"

Reviewed on Jul 10, 2025

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$179 nightly
The price is $210 total per night from Jul 27 to Jul 28
$210 total
Jul 27 - Jul 28
Total includes taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,936 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
$161 nightly
The price is $189 total per night from Aug 10 to Aug 11
$189 total
Aug 10 - Aug 11
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,008 reviews)
"Very clean and the night desk gentleman Maurice was awesome 15/10."

Reviewed on Jul 11, 2025

Holiday Inn & Suites Chicago - Downtown 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
$179 nightly
The price is $210 total per night from Jul 27 to Jul 28
$210 total
Jul 27 - Jul 28
Total includes taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,936 reviews)
"Historical place to stay if in Chicago"

Reviewed on Jul 10, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
$231 nightly
The price is $266 total per night from Aug 10 to Aug 11
$266 total
Aug 10 - Aug 11
Total includes taxes and fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,026 reviews)
"The staff at the hotel were betong top notch. It's right in the middle of everything, we were able to walk to every activity. We never felt unsafe either."

Reviewed on Jul 12, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
$151 nightly
The price is $178 total per night from Aug 10 to Aug 11
$178 total
Aug 10 - Aug 11
Total includes 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! (2,428 reviews)
"Staff is very friendly. Great location, reasonably priced. Only complaint was that the pool is not open due to renovation."

Reviewed on Jul 12, 2025

Hilton Chicago/Magnificent Mile 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.

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
$57 nightly
The price is $64 total per night from Jul 27 to Jul 28
$64 total
Jul 27 - Jul 28
Total includes 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! (1,531 reviews)
"Good"

Reviewed on Jul 9, 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 Jul 14 to Jul 15
$106 total
Jul 14 - Jul 15
Total includes taxes and fees
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
7/10 Good! (1,011 reviews)
"..."

Reviewed on Jul 9, 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
$96 nightly
The price is $109 total per night from Jul 20 to Jul 21
$109 total
Jul 20 - Jul 21
Total includes taxes and fees
Stay at this 3-star 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! (2,543 reviews)
"I Iiked Cleanliness, staff & service, property"

Reviewed on Jul 6, 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
$127 nightly
The price is $149 total per night from Aug 6 to Aug 7
$149 total
Aug 6 - Aug 7
Total includes taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,061 reviews)
"Great staff. Great hot"

Reviewed on Jul 12, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
$126 nightly
The price is $148 total per night from Aug 4 to Aug 5
$148 total
Aug 4 - Aug 5
Total includes 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 ...
7/10 Good! (2,227 reviews)
"This hotel is old and needs updated. The ac is a window unit and the heater was a standalone in the room. It felt almost like and old New York City apartment. It was fairly clean however. The price was very affordable and it was only a block from the subway. The staff was excellent. The woman who ..."

Reviewed on Jul 9, 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
$57 nightly
The price is $64 total per night from Jul 27 to Jul 28
$64 total
Jul 27 - Jul 28
Total includes 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! (1,531 reviews)
"Good"

Reviewed on Jul 9, 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
$224 nightly
The price is $263 total per night from Aug 4 to Aug 5
$263 total
Aug 4 - Aug 5
Total includes taxes and fees
Stay at this 4-star 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! (2,730 reviews)
"Hotel and breakfast was very good"

Reviewed on Jul 10, 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
$207 nightly
The price is $239 total per night from Aug 4 to Aug 5
$239 total
Aug 4 - Aug 5
Total includes taxes and fees
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,779 reviews)
"The reception area and ceilings. I’ve been going to the Palmer since 1965. This time with wife celebrating our 54th wedding anniversary. Just a wonderful place to stay. Only complaint is the price of cocktails. Two house old fashions with tax and tip costs about $50 dollars. That’s just too much ..."

Reviewed on Jul 11, 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
$211 nightly
The price is $247 total per night from Aug 10 to Aug 11
$247 total
Aug 10 - Aug 11
Total includes taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,419 reviews)
"We had a wonderful stay in Chicago."

Reviewed on Jul 11, 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
Houston
Destination Airport
Chicago
Number Of Airlines Serving
1
Distance
937 mi
Shortest Flight Departure Time
5:35AM CDT
Shortest Flight Departure Date
Jul 20

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.