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

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Cheap Flights from HOU to MDW starting at $85 One Way, $169 Round Trip

Prices starting at $169 for return flights and $85 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, Jul 29 - Tue, Aug 4
HOU
Houston
MDW
Chicago
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jul 29 from Houston to Chicago, returning Tue, Aug 4, priced at $169 found 5 days ago
Tue, Jun 9 - Wed, Jun 10
HOU
Houston
MDW
Chicago
$173 Roundtrip, found 4 days ago
$173
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Houston to Chicago, returning Wed, Jun 10, priced at $173 found 4 days ago
Wed, Jul 29 - Tue, Aug 4
HOU
Houston
MDW
Chicago
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jul 29 from Houston to Chicago, returning Tue, Aug 4, priced at $179 found 5 days ago
Tue, Jun 9 - Tue, Jun 23
HOU
Houston
MDW
Chicago
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Jun 9 from Houston to Chicago, returning Tue, Jun 23, priced at $183 found 1 day ago
Wed, Jul 29 - Tue, Aug 4
HOU
Houston
MDW
Chicago
$184 Roundtrip, found 5 days ago
$184
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Jul 29 from Houston to Chicago, returning Tue, Aug 4, priced at $184 found 5 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
$145 nightly
The price is $172 total per night from May 24 to May 25
$172 total
May 24 - May 25
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! (2,173 reviews)
Breakfast was good .. parking was ok but quite pricey considering we’re already paying to stay

Reviewed on May 11, 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
$135 nightly
The price is $161 total per night from May 12 to May 13
$161 total
May 12 - May 13
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! (10,209 reviews)
Parking lot nearby - no coffe bar - in room coffee machine didn’t work. Good location for walking to Grant Park

Reviewed on May 11, 2026

Congress Plaza Hotel
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$134 nightly
The price is $160 total per night from May 25 to May 26
$160 total
May 25 - May 26
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! (1,998 reviews)
Amazing location! We were able to walk to all local landmarks and great spots to eat. The room was very clean with an incredible view.

Reviewed on May 11, 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
$135 nightly
The price is $161 total per night from May 12 to May 13
$161 total
May 12 - May 13
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! (10,209 reviews)
Parking lot nearby - no coffe bar - in room coffee machine didn’t work. Good location for walking to Grant Park

Reviewed on May 11, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$165 nightly
The price is $197 total per night from May 25 to May 26
$197 total
May 25 - May 26
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! (4,106 reviews)
Was a really nice hotel. My only concerns was the phones in the room didn’t work. No way to call front desk, front people weren’t super helpful and there was no microwave. Rooftop bar and room were excellent

Reviewed on May 10, 2026

Hotel Riu Plaza Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$152 nightly
The price is $181 total per night from May 26 to May 27
$181 total
May 26 - May 27
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 ...
8.8/10 Excellent! (5,196 reviews)
Good for what you pay and the location can’t be beat.

Reviewed on May 11, 2026

River 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
$60 nightly
The price is $68 total per night from May 18 to May 19
$68 total
May 18 - May 19
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! (1,949 reviews)
I stayed at this motel for 7 nights, and unfortunately, my experience was very disappointing. The property was extremely dirty, including both the hallways and my room. It didn’t appear that the floors had been properly vacuumed or cleaned. The bathroom was especially concerning, with visible mold ...

Reviewed on May 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
$101 nightly
The price is $112 total per night from May 25 to May 26
$112 total
May 25 - May 26
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! (1,412 reviews)
Very nice staff!!! Hotel smelled and looked clean! Stayed for two days when I left my room they cleaned our room with us asking and gave us towels

Reviewed on May 11, 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
$93 nightly
The price is $107 total per night from May 25 to May 26
$107 total
May 25 - May 26
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 ...
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
$95 nightly
The price is $113 total per night from May 25 to May 26
$113 total
May 25 - May 26
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! (2,976 reviews)
Dirty, rude, extremely small room with nothing but a barely working tv.

Reviewed on May 11, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$118 nightly
The price is $140 total per night from May 27 to May 28
$140 total
May 27 - May 28
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! (2,600 reviews)
It was convenient location. The only negative was the noise from the street. The windows are old and can't be opened. The radiator clanks a lot at night making it difficult to sleep.

Reviewed on May 11, 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
$60 nightly
The price is $68 total per night from May 18 to May 19
$68 total
May 18 - May 19
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! (1,949 reviews)
I stayed at this motel for 7 nights, and unfortunately, my experience was very disappointing. The property was extremely dirty, including both the hallways and my room. It didn’t appear that the floors had been properly vacuumed or cleaned. The bathroom was especially concerning, with visible mold ...

Reviewed on May 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
$176 nightly
The price is $209 total per night from May 25 to May 26
$209 total
May 25 - May 26
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! (2,859 reviews)
The downside of this location is it takes longer to get to train stations otherwise if you’re not using the train it is a good location

Reviewed on May 11, 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
$168 nightly
The price is $199 total per night from May 25 to May 26
$199 total
May 25 - May 26
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! (2,439 reviews)
My favorite place to stay!

Reviewed on May 11, 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
$163 nightly
The price is $194 total per night from May 25 to May 26
$194 total
May 25 - May 26
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! (5,954 reviews)
I thoroughly enjoyed my stay at this hotel. The room was exceptionally comfortable, and every aspect of my experience was positive. I am confident that I will return to this hotel in the future.

Reviewed on May 11, 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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