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

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Cheap Flights from HOU to MDW starting at $88 One Way, $183 Round Trip

Prices starting at $183 for return flights and $88 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.

Thu, Sep 17 - Mon, Sep 21
HOU
Houston
MDW
Chicago
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Sep 17 from Houston to Chicago, returning Mon, Sep 21, priced at $183 found 5 days ago
Sat, Sep 12 - Mon, Sep 14
HOU
Houston
MDW
Chicago
$186 Roundtrip, found 2 days ago
$186
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Sep 12 from Houston to Chicago, returning Mon, Sep 14, priced at $186 found 2 days ago
Wed, Sep 16 - Sat, Sep 19
HOU
Houston
MDW
Chicago
$191 Roundtrip, found 3 days ago
$191
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Sep 16 from Houston to Chicago, returning Sat, Sep 19, priced at $191 found 3 days ago
Wed, Oct 14 - Thu, Oct 15
HOU
Houston
MDW
Chicago
$193 Roundtrip, found 2 days ago
$193
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Houston to Chicago, returning Thu, Oct 15, priced at $193 found 2 days ago
Thu, Sep 17 - Mon, Sep 21
HOU
Houston
MDW
Chicago
$196 Roundtrip, found 5 days ago
$196
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Sep 17 from Houston to Chicago, returning Mon, Sep 21, priced at $196 found 5 days 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
$237 nightly
The price is $281 total per night from Aug 10 to Aug 11
$281 total
Aug 10 - Aug 11
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! (1,228 reviews)
"Great"

Reviewed on Jul 26, 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
$176 nightly
The price is $209 total per night from Aug 20 to Aug 21
$209 total
Aug 20 - Aug 21
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 ...
Holiday Inn & Suites Chicago - Downtown by IHG
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
$176 nightly
The price is $210 total per night from Aug 20 to Aug 21
$210 total
Aug 20 - Aug 21
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! (2,427 reviews)
"Good"

Reviewed on Jul 26, 2026

Crowne Plaza Chicago West Loop 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
$170 nightly
The price is $202 total per night from Aug 10 to Aug 11
$202 total
Aug 10 - Aug 11
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
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$172 nightly
The price is $204 total per night from Aug 9 to Aug 10
$204 total
Aug 9 - Aug 10
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 ...
8.2/10 Very Good! (1,856 reviews)
"Staff were excellent. Hotel was kind of dingy. Breakfast outrageously expensive."

Reviewed on Jul 26, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$199 nightly
The price is $227 total per night from Aug 6 to Aug 7
$227 total
Aug 6 - Aug 7
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 ...
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 Aug 11 to Aug 12
$73 total
Aug 11 - Aug 12
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! (1,988 reviews)
"This was the dirtiest hotel I've ever stayed at. Carpet in hall ways were especially dirty. Not even vacuumed. Hotel itself was very run down, outdated and dirty! Beds are literally a metal frame with a very skinny uncomfortable mattress. Not happy for the price I paid!"

Reviewed on Jul 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
$99 nightly
The price is $110 total per night from Aug 24 to Aug 25
$110 total
Aug 24 - Aug 25
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! (1,631 reviews)
"Great Breakfast menu and good hot tub"

Reviewed on Jul 27, 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 Aug 23 to Aug 24
$107 total
Aug 23 - Aug 24
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
$142 nightly
The price is $168 total per night from Aug 24 to Aug 25
$168 total
Aug 24 - Aug 25
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! (3,228 reviews)
"Great customer service, the bartender was fantastic and fun!"

Reviewed on Jul 26, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$148 nightly
The price is $175 total per night from Aug 16 to Aug 17
$175 total
Aug 16 - Aug 17
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 ...
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 Aug 11 to Aug 12
$73 total
Aug 11 - Aug 12
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! (1,988 reviews)
"This was the dirtiest hotel I've ever stayed at. Carpet in hall ways were especially dirty. Not even vacuumed. Hotel itself was very run down, outdated and dirty! Beds are literally a metal frame with a very skinny uncomfortable mattress. Not happy for the price I paid!"

Reviewed on Jul 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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
$249 nightly
The price is $297 total per night from Aug 9 to Aug 10
$297 total
Aug 9 - Aug 10
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! (2,549 reviews)
"Convenient loop location."

Reviewed on Jul 27, 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
$187 nightly
The price is $222 total per night from Aug 16 to Aug 17
$222 total
Aug 16 - Aug 17
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
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
$280 nightly
The price is $333 total per night from Aug 23 to Aug 24
$333 total
Aug 23 - Aug 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hyatt Regency 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.

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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