Cheap flights from IAH to MDW (George Bush Intercontinental to Midway Intl.)

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Cheap Flights from IAH to MDW starting at $41 One Way, $81 Round Trip

Prices starting at $81 for return flights and $41 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, May 14 - Wed, May 21
IAH
Houston
MDW
Chicago
$81 Roundtrip, found 5 days ago
$81
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 14 from Houston to Chicago, returning Wed, May 21, priced at $81 found 5 days ago
Wed, May 7 - Fri, May 16
IAH
Houston
MDW
Chicago
$100 Roundtrip, found 6 days ago
$100
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 7 from Houston to Chicago, returning Fri, May 16, priced at $100 found 6 days ago
Wed, May 21 - Mon, Jun 2
IAH
Houston
MDW
Chicago
$124 Roundtrip, found 13 hours ago
$124
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Wed, May 21 from Houston to Chicago, returning Mon, Jun 2, priced at $124 found 13 hours ago
Wed, May 21 - Fri, May 30
IAH
Houston
MDW
Chicago
$126 Roundtrip, found 6 days ago
$126
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 21 from Houston to Chicago, returning Fri, May 30, priced at $126 found 6 days ago
Wed, May 7 - Mon, May 12
IAH
Houston
MDW
Chicago
$131 Roundtrip, found 6 days ago
$131
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 7 from Houston to Chicago, returning Mon, May 12, priced at $131 found 6 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
The price is $129 per night from May 26 to May 27
$129
includes taxes & fees
$110 per night
May 26 - May 27
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,019 reviews)
"Nice location"

Reviewed on Apr 28, 2025

Crowne Plaza Chicago West Loop by IHG
Sonder South Wabash
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
The price is $132 per night from May 26 to May 27
$132
includes taxes & fees
$112 per night
May 26 - May 27
Stay at this 3.5-star aparthotel in Chicago. Enjoy a fitness center, concierge services, and in-room washers/dryers. Popular attractions Soldier Field and Grant ...
8.8/10 Excellent! (484 reviews)
Enjoyable stay
"Decent studio apartment with a well stocked kitchen. Secure building, easy access with codes. Walkable to train and soldier field. Comfy bed, decent sized bathroom. Some noise in hall (doors, people talking) as expected but otherwise fairly quite building. We could hear the train but it didn’t disrupt ..."

Reviewed on Apr 24, 2025

Sonder South Wabash
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
The price is $154 per night from May 4 to May 5
$154
includes taxes & fees
$131 per night
May 4 - May 5
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8/10 Very Good! (1,000 reviews)
"The floors were dirty as if they don't even mop....not really close to anything....construction is going on"

Reviewed on Apr 29, 2025

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

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
The price is $189 per night from May 11 to May 12
$189
includes taxes & fees
$161 per night
May 11 - May 12
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,962 reviews)
"Housemaid cleaned only twice during my 4 overnight stays"

Reviewed on Apr 30, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $168 per night from May 12 to May 13
$168
includes taxes & fees
$143 per night
May 12 - May 13
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,733 reviews)
"Really nice hotel next to millennium park."

Reviewed on Apr 28, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $188 per night from May 11 to May 12
$188
includes taxes & fees
$160 per night
May 11 - May 12
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 ...
8.8/10 Excellent! (2,163 reviews)
"Nice place to stay ! Walkable to the Michigan AVE where everything is. Quiet stay was lovely."

Reviewed on Apr 29, 2025

Hilton Chicago/Magnificent Mile Suites
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
The price is $62 per night from May 1 to May 2
$62
includes taxes & fees
$55 per night
May 1 - May 2
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! (1,426 reviews)
"Easy check in and staff was friendly !"

Reviewed on Apr 30, 2025

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
The price is $102 per night from May 4 to May 5
$102
includes taxes & fees
$92 per night
May 4 - May 5
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
6.8/10 (1,002 reviews)
"Very well kept hotel"

Reviewed on Apr 28, 2025

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
The price is $101 per night from May 14 to May 15
$101
includes taxes & fees
$88 per night
May 14 - May 15
Stay at this 3-star 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! (2,461 reviews)
"Very easy to navigate! And the bed was so comfortable! Clean room and there were stores conveniently within walking distance. Next door."

Reviewed on Apr 27, 2025

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
The price is $117 per night from May 26 to May 27
$117
includes taxes & fees
$100 per night
May 26 - May 27
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (1,753 reviews)
"Perfect Location for the Magnificent mile, reasonable prices, friendly staff. Smaller rooms but couldn’t beat the price. Walking distance from everything the Navy Pier, the river walk, shopping, and authentic Chicago signature dishes…will stay here again"

Reviewed on Apr 29, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2 out of 5
65 E Harrison St, Chicago, IL
The price is $110 per night from May 1 to May 2
$110
includes taxes & fees
$94 per night
May 1 - May 2
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 ...
6.8/10 (2,108 reviews)
"Great location for walking"

Reviewed on Apr 29, 2025

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
The price is $62 per night from May 1 to May 2
$62
includes taxes & fees
$55 per night
May 1 - May 2
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! (1,426 reviews)
"Easy check in and staff was friendly !"

Reviewed on Apr 30, 2025

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
The price is $210 per night from May 11 to May 12
$210
includes taxes & fees
$179 per night
May 11 - May 12
Stay at this 4-star 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! (2,649 reviews)
"Continental breakfast was amazing.. Friendly staff. Location was walking distance to Riverboat rides."

Reviewed on Apr 29, 2025

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
The price is $194 per night from May 26 to May 27
$194
includes taxes & fees
$169 per night
May 26 - May 27
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,704 reviews)
"This is a lovely older hotel"

Reviewed on Apr 30, 2025

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
The price is $189 per night from May 11 to May 12
$189
includes taxes & fees
$161 per night
May 11 - May 12
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,962 reviews)
"Housemaid cleaned only twice during my 4 overnight stays"

Reviewed on Apr 30, 2025

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.

IAH to MDW Route Info

Origin Airport
Houston
Destination Airport
Chicago
Number Of Airlines Serving
1
Distance
918 mi
Shortest Flight Departure Time
10:40AM CDT
Shortest Flight Departure Date
May 7
IAH Address & GPS
Address:
16930 JFK Boulevard
Houston TX, 77032
United States
IATA Code:
IAH
Longitude:
-95.34
Latitude:
29.983333
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

Am I able to catch a flight from Houston, TX Airport (IAH-George Bush Intercontinental) to Chicago, IL Airport (MDW-Midway Intl.) now?
Our Covid-19 Travel Advisor will help you with queries about travel restrictions and quarantine requirements when catching a flight from Houston, TX Airport (IAH-George Bush Intercontinental) to Chicago, IL Airport (MDW-Midway Intl.).
Are there non-stop flights from Houston, TX Airport (IAH-George Bush Intercontinental) to MDW?
Whether you’re heading off on an epic worldwide adventure or traveling for work-related purposes, a nonstop flight is the best way to go. With Southwest Airlines you can fly from George Bush Intercontinental Airport (IAH) to Midway Airport in one simple journey.
What is the shortest flight from Houston Airport to Chicago Airport?
The fastest flight from George Bush Intercontinental Airport (IAH) to Chicago Airport is 4 hours and 33 minutes. Bring something extra to keep you occupied, like an interesting read or a portable board game.
How many hours flight from Houston Airport to Chicago Airport?
Settle in and get comfortable, because the average flight time from Houston Airport to MDW is 4 hours and 39 minutes. Watch a movie or two, finally finish that book … You’ll have plenty of time to relax and unwind.
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago, IL Airport (MDW-Midway Intl.)?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago, IL Airport (MDW-Midway Intl.) have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago, IL Airport (MDW-Midway Intl.) with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago, IL Airport (MDW-Midway Intl.) without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What airlines have the most flights from Houston Airport to Chicago Airport?
Southwest Airlines is your ticket to an amazing vacation. This renowned airline offers 112 flights each month from Brookhollow to West Lawn.

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.