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

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Cheap Flights from HOU to MDW starting at $86 One Way, $171 Round Trip

Prices starting at $171 for return flights and $86 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.

Wed, Sep 2 - Wed, Sep 16
HOU
Houston
MDW
Chicago
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Houston to Chicago, returning Wed, Sep 16, priced at $171 found 1 day ago
Wed, Sep 2 - Wed, Sep 16
HOU
Houston
MDW
Chicago
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Houston to Chicago, returning Wed, Sep 16, priced at $177 found 1 day ago
Wed, Sep 2 - Wed, Sep 16
HOU
Houston
MDW
Chicago
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Houston to Chicago, returning Wed, Sep 16, priced at $180 found 1 day ago
Wed, Sep 2 - Wed, Sep 16
HOU
Houston
MDW
Chicago
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Houston to Chicago, returning Wed, Sep 16, priced at $181 found 1 day ago
Wed, Jul 1 - Wed, Jul 15
HOU
Houston
MDW
Chicago
$185 Roundtrip, found 19 hours ago
$185
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Wed, Jul 1 from Houston to Chicago, returning Wed, Jul 15, priced at $185 found 19 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
$324 nightly
The price is $385 total per night from Jun 7 to Jun 8
$385 total
Jun 7 - Jun 8
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! (1,090 reviews)
"Second time staying in this hotel and it never disappoints. EVERY staff member was extremely nice."

Reviewed on May 27, 2026

Hyatt Regency McCormick Place Chicago
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
$218 nightly
The price is $259 total per night from Jun 11 to Jun 12
$259 total
Jun 11 - Jun 12
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! (2,217 reviews)
"The parking situation was terrible. At check-in, our room was not even ready. Once we finally got into the room, it was very dirty. There was hair in the bed, ashes from smoking, and crumbs all over the carpet. The carpet had clearly not been vacuumed at all."

Reviewed on May 26, 2026

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$188 nightly
The price is $223 total per night from Jun 3 to Jun 4
$223 total
Jun 3 - Jun 4
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! (10,145 reviews)
"Very good location right in the heart of Downtown Chicago."

Reviewed on May 26, 2026

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.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$188 nightly
The price is $223 total per night from Jun 3 to Jun 4
$223 total
Jun 3 - Jun 4
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! (10,145 reviews)
"Very good location right in the heart of Downtown Chicago."

Reviewed on May 26, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$251 nightly
The price is $298 total per night from Jun 16 to Jun 17
$298 total
Jun 16 - Jun 17
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,263 reviews)
"The staff is very helpful, always ready to answer any question about the hotel or about the city of Chicago. The hotel is very clean , the breakfast is very good with many choices and the staff in the restaurant is excellent. My wife and I stayed in that place for eight days and seven nights and ..."

Reviewed on May 27, 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$192 nightly
The price is $229 total per night from Jun 16 to Jun 17
$229 total
Jun 16 - Jun 17
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,476 reviews)
"Everything"

Reviewed on May 27, 2026

The Chicago Hotel Collection - Magnificent Mile
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 May 28 to May 29
$62 total
May 28 - May 29
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! (1,931 reviews)
"Pros: Free parking, fairly low price on short notice. Inside of room was clean enough, in decent enough repair, didn't smell bad or anything, plenty of space, large bed which was comfortable enough. Once there, staff seemed pleasant enough. Cons: When I called the hotel directly the evening I booked, ..."

Reviewed on May 26, 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
$103 nightly
The price is $114 total per night from Jun 21 to Jun 22
$114 total
Jun 21 - Jun 22
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 ...
7.6/10 Good! (1,444 reviews)
"Convenient to airport. Appreciated having the airport shuttle."

Reviewed on May 26, 2026

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
$104 nightly
The price is $120 total per night from May 28 to May 29
$120 total
May 28 - May 29
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! (3,015 reviews)
"Easy access to food and shuttle to airport."

Reviewed on May 27, 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
$164 nightly
The price is $195 total per night from Jun 10 to Jun 11
$195 total
Jun 10 - Jun 11
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! (3,033 reviews)
"I honestly dont have any complaints. it is an older hotel but it was still pleasant and clean."

Reviewed on May 26, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$161 nightly
The price is $192 total per night from Jun 3 to Jun 4
$192 total
Jun 3 - Jun 4
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! (2,609 reviews)
"The good: The staff was incredible, friendly and helpful. The location can hardly be beat. The building felt very secure. The bad: no fridge or microwave in the room. And the bathroom was so small that a larger person would have difficulty completing important bodily tasks. (The toilet is so close ..."

Reviewed on May 26, 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 May 28 to May 29
$62 total
May 28 - May 29
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! (1,931 reviews)
"Pros: Free parking, fairly low price on short notice. Inside of room was clean enough, in decent enough repair, didn't smell bad or anything, plenty of space, large bed which was comfortable enough. Once there, staff seemed pleasant enough. Cons: When I called the hotel directly the evening I booked, ..."

Reviewed on May 26, 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
$278 nightly
The price is $331 total per night from Jun 11 to Jun 12
$331 total
Jun 11 - Jun 12
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! (2,857 reviews)
"Hotel is in a good area for walking to places. Walls are paper thin heard sirens all night plus a baby in the other room crying all night. Elevators at one point only one elevator was available for the whole hotel and then only two which made getting to your room very hard. The breakfast and happy ..."

Reviewed on May 26, 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
$307 nightly
The price is $365 total per night from Jun 21 to Jun 22
$365 total
Jun 21 - Jun 22
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! (2,457 reviews)
"Beautiful place to stay."

Reviewed on May 26, 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
$220 nightly
The price is $261 total per night from Jun 14 to Jun 15
$261 total
Jun 14 - Jun 15
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! (5,940 reviews)
"Was decent"

Reviewed on May 26, 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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