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

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Cheap Flights from HOU to MDW starting at $105 One Way, $214 Round Trip

Prices starting at $214 for return flights and $105 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.

Tue, Aug 4 - Wed, Aug 5
HOU
Houston
MDW
Chicago
$214 Roundtrip, found 6 days ago
$214
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Aug 4 from Houston to Chicago, returning Wed, Aug 5, priced at $214 found 6 days ago
Sat, Sep 26 - Thu, Oct 8
HOU
Houston
MDW
Chicago
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Sep 26 from Houston to Chicago, returning Thu, Oct 8, priced at $217 found 2 days ago
Wed, Sep 23 - Sat, Sep 26
HOU
Houston
MDW
Chicago
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Sep 23 from Houston to Chicago, returning Sat, Sep 26, priced at $219 found 2 days ago
Sat, Aug 8 - Mon, Aug 10
HOU
Houston
MDW
Chicago
$222 Roundtrip, found 14 hours ago
$222
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Sat, Aug 8 from Houston to Chicago, returning Mon, Aug 10, priced at $222 found 14 hours ago
Tue, Aug 4 - Wed, Aug 5
HOU
Houston
MDW
Chicago
$224 Roundtrip, found 6 days ago
$224
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Aug 4 from Houston to Chicago, returning Wed, Aug 5, priced at $224 found 6 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

2.5 out of 5
1622 W Jackson Blvd Chicago IL
$127 nightly
The price is $151 total per night from Jul 5 to Jul 6
$151 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,104 reviews)
"A nice surprise! Enjoyed our stay. We will be back!"

Reviewed on Jun 21, 2026

Hotel Chicago West Loop, SureStay Collection by Best Western
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$228 nightly
The price is $271 total per night from Jul 8 to Jul 9
$271 total
Jul 8 - Jul 9
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! (1,148 reviews)
"Parking was a bit of a cluster, but the line moved quickly to get checked into our room. Overall great experience"

Reviewed on Jun 22, 2026

Hyatt Regency McCormick Place Chicago
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$159 nightly
The price is $190 total per night from Jul 1 to Jul 2
$190 total
Jul 1 - Jul 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,039 reviews)
"Way overpriced for what you get."

Reviewed on Jun 21, 2026

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
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
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! (10,163 reviews)
"The room was very clean and the staff were fantastic! I would recommend this hotel to anyone it was close to all the public transit stations"

Reviewed on Jun 22, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$139 nightly
The price is $166 total per night from Jul 1 to Jul 2
$166 total
Jul 1 - Jul 2
Total with 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 ...
9/10 Wonderful! (4,461 reviews)
"A very easily accessible location, close to many eateries and especially the magnificent mile!"

Reviewed on Jun 22, 2026

Hilton Chicago/Magnificent Mile Suites
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$127 nightly
The price is $145 total per night from Jun 28 to Jun 29
$145 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,714 reviews)
"This property is really nice. The staff aren’t too friendly and they charge for everything. Literally. There were two bottles of water in our room $4 a piece . I’m not concerned about the price but one was definitely open and half way gone so I hope that’s not going to be charged to our room as we ..."

Reviewed on Jun 22, 2026

Hyatt Regency O'Hare 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
$65 nightly
The price is $73 total per night from Jul 7 to Jul 8
$73 total
Jul 7 - Jul 8
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! (1,963 reviews)
"You get what you pay for. It was great for the price. Good friendly cleaning staff, beds were hard and you sink to the middle. Other than that no issues. Can’t complain"

Reviewed on Jun 22, 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
$112 nightly
The price is $124 total per night from Jun 29 to Jun 30
$124 total
Jun 29 - Jun 30
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! (1,523 reviews)
"Amazing"

Reviewed on Jun 22, 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
$100 nightly
The price is $115 total per night from Jun 29 to Jun 30
$115 total
Jun 29 - Jun 30
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! (3,026 reviews)
"The property was clean. Breakfast is in the restaurant and had decent options. Water and coffee available all day. The shuttle is a bit weird in that you have to sign up for it. The shuttle is pretty fast for a pickup from the blue line."

Reviewed on Jun 22, 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
$145 nightly
The price is $172 total per night from Jul 5 to Jul 6
$172 total
Jul 5 - Jul 6
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! (3,114 reviews)
"I stayed for four nights in a room with a queen bed, and there were a lot of issues with the stay: I had to stay on top of the staff to make sure I got the items I needed. When I arrived, the bathroom shower soap was out. I asked the front desk three times for them to send someone to refill it. I ..."

Reviewed on Jun 22, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$123 nightly
The price is $147 total per night from Jul 5 to Jul 6
$147 total
Jul 5 - Jul 6
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! (2,637 reviews)
"The Wyndam in Chicago is a budget hotel with limited amenities. I'll do in a pinch, but there are a lot of better hotels in the area."

Reviewed on Jun 22, 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
$65 nightly
The price is $73 total per night from Jul 7 to Jul 8
$73 total
Jul 7 - Jul 8
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! (1,963 reviews)
"You get what you pay for. It was great for the price. Good friendly cleaning staff, beds were hard and you sink to the middle. Other than that no issues. Can’t complain"

Reviewed on Jun 22, 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
$221 nightly
The price is $262 total per night from Jul 6 to Jul 7
$262 total
Jul 6 - Jul 7
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! (2,880 reviews)
"Staff were wonderful and quick to help. When we checked in Abraham was so helpful! From a long drive and the chaos of getting into the city, he helped ensure that I got checked in properly and explain the parking situation and daily vouchers!"

Reviewed on Jun 22, 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 $248 total per night from Jun 30 to Jul 1
$248 total
Jun 30 - Jul 1
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! (2,495 reviews)
"Prepaid parking through Expedia not honored at the hotel. Staff completely unhelpful in sorting this issue out. Forced to double pay for parking. Rooms dated with older furnishings. Beds old. Plumbing drained poorly. Location nice but otherwise I would not recommend."

Reviewed on Jun 22, 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
$148 nightly
The price is $176 total per night from Jul 5 to Jul 6
$176 total
Jul 5 - Jul 6
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! (5,992 reviews)
"Great place, we will come back to this hotel soon!"

Reviewed on Jun 22, 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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