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

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Cheap Flights from HOU to MDW starting at $123 One Way, $209 Round Trip

Prices starting at $209 for return flights and $123 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.

Mon, Sep 21 - Wed, Sep 23
HOU
Houston
MDW
Chicago
$209 Roundtrip, found 5 days ago
$209
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 21 from Houston to Chicago, returning Wed, Sep 23, priced at $209 found 5 days ago
Mon, Sep 21 - Wed, Sep 23
HOU
Houston
MDW
Chicago
$218 Roundtrip, found 5 days ago
$218
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 21 from Houston to Chicago, returning Wed, Sep 23, priced at $218 found 5 days ago
Mon, Sep 21 - Wed, Sep 23
HOU
Houston
MDW
Chicago
$219 Roundtrip, found 5 days ago
$219
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 21 from Houston to Chicago, returning Wed, Sep 23, priced at $219 found 5 days ago
Mon, Sep 21 - Wed, Sep 23
HOU
Houston
MDW
Chicago
$225 Roundtrip, found 5 days ago
$225
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Sep 21 from Houston to Chicago, returning Wed, Sep 23, priced at $225 found 5 days ago
Mon, Oct 12 - Wed, Oct 14
HOU
Houston
MDW
Chicago
$231 Roundtrip, found 5 days ago
$231
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Oct 12 from Houston to Chicago, returning Wed, Oct 14, priced at $231 found 5 days 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
$141 nightly
The price is $164 total per night from Sep 7 to Sep 8
$164 total
Sep 7 - Sep 8
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 ...
8.2/10 Very Good! (1,017 reviews)
"I kept trying to figure out why I had so many mosquito bites when I didn’t spend much time outside and when I was getting them because they just seemed to appear overnight. When we were packing up to leave during our last morning, I told my mom I needed to get something for all my itchy bites, mostly ..."

Reviewed on Sep 1, 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
$95 nightly
The price is $113 total per night from Sep 8 to Sep 9
$113 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! (10,243 reviews)
"Beautiful building. Clean room and fairly spacious. Bed wasn't super comfortable but it was fine for 2 night stay. The elevators were fast and we had a small view of the lake and Michigan Ave. Super convenient location with lots of food choices within short walk. Easy walk to museum center and Soldier ..."

Reviewed on Sep 1, 2026

Congress Plaza Hotel
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$244 nightly
The price is $290 total per night from Sep 2 to Sep 3
$290 total
Sep 2 - Sep 3
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! (1,360 reviews)
".."

Reviewed on Sep 1, 2026

Hyatt Regency McCormick Place 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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$95 nightly
The price is $113 total per night from Sep 8 to Sep 9
$113 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! (10,243 reviews)
"Beautiful building. Clean room and fairly spacious. Bed wasn't super comfortable but it was fine for 2 night stay. The elevators were fast and we had a small view of the lake and Michigan Ave. Super convenient location with lots of food choices within short walk. Easy walk to museum center and Soldier ..."

Reviewed on Sep 1, 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
$122 nightly
The price is $144 total per night from Sep 8 to Sep 9
$144 total
Sep 8 - Sep 9
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! (2,144 reviews)
"Need to take those carpets out and clean bugs off of curtains and shower. Disgusted me slightly"

Reviewed on Sep 1, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Get rates
Kasa Magnificent Mile 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.

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 1 to Oct 2
$60 total
Oct 1 - Oct 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! (2,004 reviews)
"The laminate floors where all popping and you kept tripping on them. Bathroom was no better. Seemed a little runned down."

Reviewed on Sep 1, 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
$106 nightly
The price is $117 total per night from Sep 7 to Sep 8
$117 total
Sep 7 - Sep 8
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! (1,726 reviews)
"Great experience. Loved the premises. Friendly staff great Beakfast and they have a nice pool and hot tub."

Reviewed on Sep 1, 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 Sep 28 to Sep 29
$107 total
Sep 28 - Sep 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 ...
7.8/10 Good! (3,157 reviews)
"Has bed bugs"

Reviewed on Aug 31, 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
$193 nightly
The price is $229 total per night from Sep 8 to Sep 9
$229 total
Sep 8 - Sep 9
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
$141 nightly
The price is $166 total per night from Sep 8 to Sep 9
$166 total
Sep 8 - Sep 9
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! (2,818 reviews)
"It was ok for a day trip"

Reviewed on Aug 31, 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 1 to Oct 2
$60 total
Oct 1 - Oct 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! (2,004 reviews)
"The laminate floors where all popping and you kept tripping on them. Bathroom was no better. Seemed a little runned down."

Reviewed on Sep 1, 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
$170 nightly
The price is $227 total per night from Sep 10 to Sep 11
$227 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! (2,987 reviews)
"Room was spacious! So close to the Mag Mile and had a Whole Foods across the street for any grocery needs! Close to shops and restaurants. And the breakfast was wonderful! Will happily stay again!"

Reviewed on Sep 1, 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
$209 nightly
The price is $246 total per night from Sep 7 to Sep 8
$246 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 ...
8.6/10 Excellent! (2,616 reviews)
"The stay was good, while I appreciate the historic and vintage feel, I realized I enjoy more modern features in a stay. The cleanliness was not great either. The staff was friendly and helpful."

Reviewed on Sep 1, 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
$145 nightly
The price is $172 total per night from Sep 7 to Sep 8
$172 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! (6,016 reviews)
"Rooms were a bit noisy from street noise, traffic at night and garbage pick up in the am. Breakfast including coffee closes very promptly, no exceptions. Daily housekeeping was hit and miss as to if they showed up and what they did each day, not consistent. Check in was seamless. GREAT central location. ..."

Reviewed on Sep 1, 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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