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

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Cheap Flights from HOU to MDW starting at $106 One Way, $210 Round Trip

Prices starting at $210 for return flights and $106 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.

Sat, Dec 12 - Wed, Dec 16
HOU
Houston
MDW
Chicago
$210 Roundtrip, found 14 hours ago
$210
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Sat, Dec 12 from Houston to Chicago, returning Wed, Dec 16, priced at $210 found 14 hours ago
Sat, Dec 12 - Wed, Dec 16
HOU
Houston
MDW
Chicago
$215 Roundtrip, found 14 hours ago
$215
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Sat, Dec 12 from Houston to Chicago, returning Wed, Dec 16, priced at $215 found 14 hours ago
Sat, Dec 12 - Wed, Dec 16
HOU
Houston
MDW
Chicago
$221 Roundtrip, found 14 hours ago
$221
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Sat, Dec 12 from Houston to Chicago, returning Wed, Dec 16, priced at $221 found 14 hours ago
Sat, Dec 12 - Wed, Dec 16
HOU
Houston
MDW
Chicago
$225 Roundtrip, found 14 hours ago
$225
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Sat, Dec 12 from Houston to Chicago, returning Wed, Dec 16, priced at $225 found 14 hours ago
Sat, Jan 16 - Wed, Jan 20
HOU
Houston
MDW
Chicago
$230 Roundtrip, found 9 hours ago
$230
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Sat, Jan 16 from Houston to Chicago, returning Wed, Jan 20, priced at $230 found 9 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
$162 nightly
The price is $188 total per night from Sep 27 to Sep 28
$188 total
Sep 27 - Sep 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 and ...
8/10 Very Good! (1,014 reviews)
"Room was clean, shuttle to airport was available every half hour which was useful to take the train to downtown."

Reviewed on Sep 14, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$164 nightly
The price is $195 total per night from Sep 27 to Sep 28
$195 total
Sep 27 - Sep 28
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 ...
Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$256 nightly
The price is $304 total per night from Sep 25 to Sep 26
$304 total
Sep 25 - Sep 26
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,215 reviews)
"Lots of hidden fees when booking with Expedia. Old rooms useless meeting and ballrooms for a standard visiting tourist."

Reviewed on Sep 14, 2026

Hilton Chicago
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

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$154 nightly
The price is $183 total per night from Sep 27 to Sep 28
$183 total
Sep 27 - Sep 28
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 ...
River 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
$161 nightly
The price is $191 total per night from Sep 28 to Sep 29
$191 total
Sep 28 - Sep 29
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! (2,241 reviews)
"We stayed here over a weekend while visiting family in Chicago. The hotel was very nice and the rooms were clean and in good working order. We got the basic room and there was no coffee maker in the room. That seems to be standard in other hotels. They also do not offer room service. No breakfast ..."

Reviewed on Sep 15, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$164 nightly
The price is $195 total per night from Sep 27 to Sep 28
$195 total
Sep 27 - Sep 28
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 ...
Congress Plaza 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
$53 nightly
The price is $60 total per night from Oct 4 to Oct 5
$60 total
Oct 4 - Oct 5
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! (2,010 reviews)
"Clean room and friendly staff, outside area feels safe. I think these are the most important. Downside is no refrigerator in room. No microwave in room either but there is one in lobby downstairs."

Reviewed on Sep 14, 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
$100 nightly
The price is $110 total per night from Oct 4 to Oct 5
$110 total
Oct 4 - Oct 5
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 Oct 4 to Oct 5
$116 total
Oct 4 - Oct 5
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! (3,168 reviews)
"Ubicación y servicio"

Reviewed on Sep 14, 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
$226 nightly
The price is $268 total per night from Oct 6 to Oct 7
$268 total
Oct 6 - Oct 7
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. ...
7.8/10 Good! (3,374 reviews)
"Lots of complaints from folks in the lobby. Unhygienic place, won’t book again"

Reviewed on Sep 14, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$141 nightly
The price is $167 total per night from Sep 29 to Sep 30
$167 total
Sep 29 - Sep 30
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 ...
7.8/10 Good! (2,849 reviews)
"For the cost of stay, this hotel did not meet the standards"

Reviewed on Sep 14, 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 Oct 4 to Oct 5
$60 total
Oct 4 - Oct 5
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! (2,010 reviews)
"Clean room and friendly staff, outside area feels safe. I think these are the most important. Downside is no refrigerator in room. No microwave in room either but there is one in lobby downstairs."

Reviewed on Sep 14, 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
$272 nightly
The price is $324 total per night from Sep 27 to Sep 28
$324 total
Sep 27 - Sep 28
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 ...
8.4/10 Very Good! (3,010 reviews)
"We went there for a long weekend, and the hotel was very crowded. There was no coin laundry and the laundry service was very expensive. They gave $16 coupon for the laundry service, but it that wasn't even sufficient for two pairs of socks. The property was good enough but wasn't super clean for ..."

Reviewed on Sep 15, 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
$309 nightly
The price is $367 total per night from Sep 27 to Sep 28
$367 total
Sep 27 - Sep 28
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! (2,648 reviews)
"I loved everything in the hotel, but the most eating my breakfast in the restaurant. Also, I enjoyed my facial it was a great experience. I hope, I will come back again."

Reviewed on Sep 15, 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
$211 nightly
The price is $250 total per night from Sep 20 to Sep 21
$250 total
Sep 20 - Sep 21
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 ...
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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