$83+ Cheap flights from George Bush Intcntl (IAH) to Midway (MDW)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
IAH — MDW
Sep 2 — Sep 91
Round-trip
1 adult, Economy
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Cheapest flights from George Bush Intcntl to MidwayExplore the most affordable flight options available from George Bush Intcntl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 3, 2026.
Explore the most affordable flight options available from George Bush Intcntl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 3, 2026.
This Trip.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Tue 8/2511:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 8/2![Frontier logo]()
$170
This Orbitz deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:35 pm
IAH
- MDW
1 stop8h 23m
Frontier
Mon 10/1912:03 pm
MDW
- IAH
1 stop10h 03m
Frontier
Deal found 7/30![Frontier logo]()
$173
This Frontier deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Tue 9/811:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 8/2![Frontier logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Mon 8/2411:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 8/2![Frontier logo]()
$180
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/141:35 pm
IAH
- MDW
1 stop8h 18m
Frontier
Tue 11/177:25 am
MDW
- IAH
1 stop7h 40m
Frontier
Deal found 7/31![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:32 am
IAH
- MDW
1 stop11h 15m
Frontier
Mon 8/3111:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 7/29![Frontier logo]()
$184
This Trip.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:28 am
IAH
- MDW
1 stop11h 23m
Frontier
Sat 10/106:40 am
MDW
- IAH
1 stop6h 00m
Frontier
Deal found 7/30![Frontier logo]()
$188
This Trip.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/151:35 pm
IAH
- MDW
1 stop8h 23m
Frontier
Wed 10/216:40 am
MDW
- IAH
1 stop6h 00m
Frontier
Deal found 8/3![Frontier logo]()
$192
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Fri 9/411:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 7/31![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3011:32 am
IAH
- MDW
1 stop11h 15m
Frontier
Sat 9/511:45 am
MDW
- IAH
1 stop10h 29m
Frontier
Deal found 7/30![Frontier logo]()
$199
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/34:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Fri 9/411:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 7/30![Frontier logo]()
$201
This Frontier deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/44:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Tue 9/811:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 8/1![Frontier logo]()
$206
Best flights from George Bush Intcntl to MidwayDiscover carefully curated flight deals from George Bush Intcntl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 3, 2026.
Discover carefully curated flight deals from George Bush Intcntl to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 3, 2026.
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:44 am
IAH
- MDW
1 stop7h 35m
Delta
Tue 9/1510:48 am
MDW
- IAH
1 stop6h 44m
Delta
Deal found 7/29![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:20 am
IAH
- MDW
2 stops10h 24m
Delta
Sat 9/54:39 pm
MDW
- IAH
1 stop7h 13m
Delta
Deal found 7/30![Delta logo]()
$234
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:09 pm
IAH
- MDW
1 stop5h 27m
Delta
Fri 9/115:03 pm
MDW
- IAH
1 stop5h 02m
Delta
Deal found 7/31![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/82:44 pm
IAH
- MDW
1 stop8h 00m
Delta
Fri 9/115:03 pm
MDW
- IAH
1 stop5h 02m
Delta
Deal found 8/2![Delta logo]()
$242
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
IAH
- MDW
2 stops9h 57m
Delta
Thu 9/1011:35 am
MDW
- IAH
1 stop5h 59m
Delta
Deal found 8/2![Delta logo]()
$260
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:20 am
IAH
- MDW
1 stop7h 19m
Delta
Sat 8/221:25 pm
MDW
- IAH
2 stops10h 27m
Delta
Deal found 7/29![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:10 am
IAH
- MDW
1 stop7h 37m
Delta
Mon 11/91:22 pm
MDW
- IAH
2 stops10h 37m
Delta
Deal found 7/31![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/165:25 am
IAH
- MDW
2 stops11h 00m
Delta
Mon 1/1812:30 pm
MDW
- IAH
2 stops11h 28m
Delta
Deal found 8/2![Delta logo]()
$309
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:28 pm
IAH
- MDW
1 stop6h 28m
Delta
Sun 11/151:22 pm
MDW
- IAH
2 stops8h 49m
Delta
Deal found 7/31![Delta logo]()
$316
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:28 am
IAH
- MDW
2 stops11h 08m
Delta
Tue 9/84:30 pm
MDW
- IAH
1 stop6h 03m
Delta
Deal found 8/2![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/285:55 am
IAH
- MDW
2 stops10h 27m
Delta
Thu 12/315:35 pm
MDW
- IAH
1 stop5h 13m
Delta
Deal found 7/30![Delta logo]()
$325
Last-minute flights from George Bush Intcntl to MidwayDiscover last-minute flight deals from George Bush Intcntl to Midway. Data last updated August 3, 2026 and is based on user searches.
Discover last-minute flight deals from George Bush Intcntl to Midway. Data last updated August 3, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/184:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Thu 8/2011:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 7/30![Frontier logo]()
$217
This Expedia deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/194:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Sat 8/2211:45 am
MDW
- IAH
1 stop10h 29m
Frontier
Deal found 7/30![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Mon 8/2411:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 8/2![Frontier logo]()
$180
This Trip.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Wed 8/2611:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 7/29![Frontier logo]()
$218
This Trip.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Tue 8/2511:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 8/2![Frontier logo]()
$170
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:37 pm
IAH
- MDW
1 stop5h 59m
Delta
Wed 9/21:51 pm
MDW
- IAH
1 stop7h 45m
Delta
Deal found 7/29![Delta logo]()
$229
This Frontier deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:32 am
IAH
- MDW
1 stop11h 15m
Frontier
Mon 8/3111:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 7/29![Frontier logo]()
$184
This Expedia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:32 am
IAH
- MDW
1 stop11h 15m
Frontier
Fri 9/411:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 7/31![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/284:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Sun 9/611:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 7/31![Frontier logo]()
$227
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Fri 9/411:50 am
MDW
- IAH
1 stop10h 24m
Frontier
Deal found 7/31![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3011:32 am
IAH
- MDW
1 stop11h 15m
Frontier
Sat 9/511:45 am
MDW
- IAH
1 stop10h 29m
Frontier
Deal found 7/30![Frontier logo]()
$199
One-way flights from George Bush Intcntl to MidwaySearch for one-way flight options from George Bush Intcntl to Midway. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
Search for one-way flight options from George Bush Intcntl to Midway. Find affordable one-way fares based on user searches. Data last updated August 3, 2026.
This Super.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:28 am
IAH
- MDW
1 stop11h 18m
Frontier
Deal found 8/1![Frontier logo]()
$83
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/211:35 pm
IAH
- MDW
1 stop8h 23m
Frontier
Deal found 7/30![Frontier logo]()
$84
This Booking.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:08 am
IAH
- MDW
1 stop11h 43m
Frontier
Deal found 7/31![Frontier logo]()
$85
This Trip.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/141:35 pm
IAH
- MDW
1 stop8h 23m
Frontier
Deal found 7/31![Frontier logo]()
$87
This Super.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:35 pm
IAH
- MDW
1 stop8h 23m
Frontier
Deal found 7/30![Frontier logo]()
$100
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/311:35 pm
IAH
- MDW
1 stop8h 18m
Frontier
Deal found 7/30![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/284:32 pm
IAH
- MDW
1 stop6h 15m
Frontier
Deal found 8/3![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:08 pm
IAH
- MDW
1 stop5h 43m
Frontier
Deal found 7/30![Frontier logo]()
$106
This Expedia deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:35 pm
IAH
- MDW
1 stop8h 23m
Frontier
Deal found 7/31![Frontier logo]()
$112
Find flight deals from George Bush Intcntl to Midway
Discover tips and strategies to find the most affordable flight options for your journey from George Bush Intcntl (IAH) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $170 (Trip.com) |
One-way from | $83 (Super.com) |
Popular in | July |
Cheapest in | April |
Average price | $263 |
Cheapflights Fare Finder
Customize your flight search to find flights from George Bush Intcntl to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 3, 2026.
Use the filters below to find and compare flights from Houston George Bush Intcntl Airport to Chicago Midway Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Wed 9/9
10:44 am-6:19 pm
1 stop7h 35m
Chicago Midway
Tue 9/15
10:48 am-5:32 pm
1 stop6h 44m
$229
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 9/1
5:20 am-3:44 pm
2 stops10h 24m
Chicago Midway
Sat 9/5
4:39 pm-11:52 pm
1 stop7h 13m
$234
Quickest round-trip
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Wed 9/2
5:09 pm-10:36 pm
1 stop5h 27m
Chicago Midway
Fri 9/11
5:03 pm-10:05 pm
1 stop5h 02m
$242
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Tue 9/8
2:44 pm-10:44 pm
1 stop8h 00m
Chicago Midway
Fri 9/11
5:03 pm-10:05 pm
1 stop5h 02m
$242
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Wed 9/9
7:00 am-4:57 pm
2 stops9h 57m
Chicago Midway
Thu 9/10
11:35 am-5:34 pm
1 stop5h 59m
$260
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Thu 8/20
5:20 am-12:39 pm
1 stop7h 19m
Chicago Midway
Sat 8/22
1:25 pm-11:52 pm
2 stops10h 27m
$269
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Fri 11/6
5:10 am-12:47 pm
1 stop7h 37m
Chicago Midway
Mon 11/9
1:22 pm-11:59 pm
2 stops10h 37m
$288
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Sat 1/16
5:25 am-4:25 pm
2 stops11h 00m
Chicago Midway
Mon 1/18
12:30 pm-11:58 pm
2 stops11h 28m
$309
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Thu 11/12
4:28 pm-10:56 pm
1 stop6h 28m
Chicago Midway
Sun 11/15
1:22 pm-10:11 pm
2 stops8h 49m
$316
HoustonChicago
IAH - MDW
IAHMDW
Houston George Bush Intcntl
Sat 9/5
11:28 am-10:36 pm
2 stops11h 08m
Chicago Midway
Tue 9/8
4:30 pm-10:33 pm
1 stop6h 03m
$319
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from George Bush Intcntl to Midway
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from George Bush Intcntl to Midway in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy2 stars | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Houston George Bush Intcntl Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Houston George Bush Intcntl Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Houston George Bush Intcntl Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Houston George Bush Intcntl Airport-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Houston George Bush Intcntl Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from George Bush Intcntl to Midway
Have a flexible travel schedule? Discover the best time to fly to Midway from George Bush Intcntl with our price prediction graph.
IAH-MDW
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Houston George Bush Intcntl Airport to Chicago Midway Airport
Prices
Delays
What is the cheapest month to book a flight from Houston George Bush Intcntl Airport to Chicago Midway Airport?
Currently, April is the cheapest month in which you can book a flight from Houston George Bush Intcntl Airport to Chicago Midway Airport (average of $94). Flying from Houston George Bush Intcntl Airport to Chicago Midway Airport in July is currently the most expensive (average of $349). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from IAH to MDW?
Find hourly flight availability from George Bush Intcntl to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 3, 2026.
One of the essential ways to save on airfare from Houston George Bush Intcntl Airport to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 34% on airfare.
How often are flights from Houston to Chicago delayed?
About 24% of weekly flights between Houston and Chicago have experienced delays in the past year, with the average delay time being 182 minutes.
What is the most punctual flight time for Houston to Chicago flights?
Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Wednesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Houston to Chicago flights?
Over the last year, Frontier have had the lowest number of delays on this route, with just 22% of flights being delayed.
The best insider tips for Houston George Bush Intcntl Airport to Chicago Midway Airport flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Houston George Bush Intcntl Airport to Chicago Midway Airport trip
Our travel experts
Reviews of airlines servicing Midway
Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated August 3, 2026.
Read through reviews of airlines operating flights from Houston George Bush Intcntl Airport to Chicago Midway Airport, such as Delta and Frontier. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentStacey-Ann,Aug 2023
IAH - ATL
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentStacey-Ann,Aug 2023
IAH - ATL
Food
7.2
Overall
7.8
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentStacey-Ann,Aug 2023
IAH - ATL
Related info for your journey
Find useful and relevant information for your journey from George Bush Intcntl to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago Midway Airport?
Book flights to Chicago Midway Airport if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Midway
Explore flights to Midway departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 3, 2026.
George Bush Intcntl and Midway flights
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Other flights from George Bush Intcntl
Browse through other flights departing from George Bush Intcntl. Flights are based on user searches made on Cheapflights and were last updated on August 3, 2026.
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Top 2 airlines flying from George Bush Intcntl to Midway
Discover the top 2 airlines that operate flights from George Bush Intcntl to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$84 | Average$163 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$216 | Average$327 | FlexibilityNo cancel fee | On-timeN/A |