$105 Find Cheap Flights from Chicago Midway Airport to Houston - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$133
Typical prices: $178-$406
Frontier
Wed 10/24Sun 10/28
MDW - IAH • 1 stop
Cheapest non-stop
$210
Typical prices: $176-$408
Southwest
Sat 12/8Sat 12/15
MDW - HOU • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 37m
Direct flights
+1
Direct flights
+1
Top routes
MDW - IAH
Cheapest • 26% average savings
MDW - HOU
Most popular
Insights
Insights
Avoid delays
Southwest
Most punctual • 80% on-time
Morning
Best time • Fewest delays
Insights
Insights
When to book
19 weeks
in advance
Our data shows that travelers who book at least 19 weeks in advance save around 27% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 32% price drop
November
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $240 (round-trip)
Dallas Love Field (DAL)
Shortest trip • 4h 37m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Houston!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Midway to Houston (MDW-HOU)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Houston

Sat, Oct 24 - Wed, Oct 28
Frontier Logo
6:21 am - 10:09 pmMDW  Chicago Midway-IAH Houston George Bush Intcntl
15h 48m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:05 am - 11:47 pmIAH  Houston George Bush Intcntl-MDW Chicago Midway
17h 42m1 stop Atlanta Hartsfield-Jackson
$133Frontier
Tue, Nov 10 - Mon, Nov 16
Frontier Logo
6:42 pm - 11:34 amMDW  Chicago Midway-IAH Houston George Bush Intcntl
16h 52m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
12:19 pm - 11:47 pmIAH  Houston George Bush Intcntl-MDW Chicago Midway
11h 28m1 stop Atlanta Hartsfield-Jackson
$148Frontier
Wed, Oct 21 - Wed, Oct 28
Frontier Logo
6:21 am - 10:23 pmMDW  Chicago Midway-IAH Houston George Bush Intcntl
16h 02m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:05 am - 5:47 pmIAH  Houston George Bush Intcntl-MDW Chicago Midway
11h 42m1 stop Atlanta Hartsfield-Jackson
$155Frontier
Tue, Dec 8 - Tue, Dec 15
Southwest Logo
6:40 am - 9:20 amMDW  Chicago Midway-HOU Houston Hobby
2h 40mnonstop
Southwest Logo
7:20 am - 9:50 amHOU  Houston Hobby-MDW Chicago Midway
2h 30mnonstop
$210Southwest
Tue, Nov 10 - Wed, Nov 18
Southwest Logo
6:40 am - 9:20 amMDW  Chicago Midway-HOU Houston Hobby
2h 40mnonstop
Southwest Logo
7:20 am - 9:50 amHOU  Houston Hobby-MDW Chicago Midway
2h 30mnonstop
$210Southwest
Wed, Oct 14 - Wed, Oct 21
Southwest Logo
7:50 am - 1:45 pmMDW  Chicago Midway-HOU Houston Hobby
5h 55m1 stop Kansas City
Southwest Logo
7:05 am - 9:30 amHOU  Houston Hobby-MDW Chicago Midway
2h 25mnonstop
$220Southwest
Wed, Nov 11 - Wed, Nov 18
Delta Logo
5:13 pm - 11:21 pmMDW  Chicago Midway-HOU Houston Hobby
6h 08m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:24 pm - 10:54 pmHOU  Houston Hobby-MDW Chicago Midway
5h 30m1 stop Atlanta Hartsfield-Jackson
$303Delta
Thu, Oct 29 - Mon, Nov 2
Delta Logo
6:04 am - 2:07 pmMDW  Chicago Midway-HOU Houston Hobby
8h 03m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:28 pm - 10:33 pmHOU  Houston Hobby-MDW Chicago Midway
5h 05m1 stop Atlanta Hartsfield-Jackson
$303Delta
Fri, Oct 16 - Sun, Oct 18
Multiple Airlines Logo
4:30 pm - 6:00 amMDW  Chicago Midway-IAH Houston George Bush Intcntl
13h 30m2 stops Knoxville McGhee Tyson Las Vegas Harry Reid Intl
Multiple Airlines Logo
12:07 pm - 5:45 pmIAH  Houston George Bush Intcntl-MDW Chicago Midway
5h 38m1 stop Atlanta Hartsfield-Jackson
$608Multiple Airlines
Sun, Oct 4 - Thu, Oct 8
Multiple Airlines Logo
6:25 am - 7:17 amMDW  Chicago Midway-IAH Houston George Bush Intcntl
24h 52m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
10:44 pm - 7:04 pmIAH  Houston George Bush Intcntl-MDW Chicago Midway
20h 20m2 stops Puebla City Huejotzingo Guadalajara Miguel Hidal
$619Multiple Airlines
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Houston flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Chicago Midway Airport to Houston with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Houston?

Round-trip flights from Chicago Midway Airport to Houston start at $133. Prices are below average for this route right now, with typical round-trip fares ranging from $178 to $406. The lowest price found in the past 5 days was $133 on Frontier.

What's the cheapest day of the week to fly from Chicago Midway Airport to Houston?

Monday is the cheapest day of the week to fly from Chicago Midway Airport to Houston, it is 10% cheaper than the average day. Sunday is the most expensive day with flight prices 25% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Chicago Midway Airport to Houston?

  • February is the cheapest month to fly from Chicago Midway Airport to Houston at $188 round-trip.
  • June ($382) and July ($379) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 103% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Chicago Midway Airport to Houston the cheapest?

Flights from Chicago Midway Airport to Houston are cheapest 19 weeks before departure. Booking in this window typically costs about 27% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals
Expert advice

Expert advice for your flight from Midway to Houston

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on Frontier

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more

Key details for Chicago Midway Airport to Houston flights

Low season

June

Cheapest flight

$105
Best time to beat the crowds but there is an average 38% increase in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Chicago Midway Airport to Houston Hobby Airport

When to book flights from Midway to Houston

Are your dates flexible? Find out the best times to travel from Midway to Houston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Houston flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to Houston flights?

    Among airlines operating Chicago Midway Airport to Houston flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • What airlines are available from Chicago Midway Airport to Houston?

    Only Southwest operates flights between Chicago Midway Airport and Houston.

  • Which airports can I use when flying from Chicago Midway Airport to Houston?

    Flights from Chicago Midway Airport to Houston usually depart from Chicago Midway (MDW) and may arrive at several airports in Houston area, including Houston Hobby (HOU) and Houston George Bush Intcntl (IAH).

  • Which airlines include bags at no extra cost on Chicago Midway Airport to Houston flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

  • What cabin classes can I book on flights from Chicago Midway Airport to Houston?

    Only Economy Class is available on flights from Chicago Midway Airport to Houston.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to Houston?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $240 round-trip via Orlando (MCO), compared to $280 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to Houston?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which airports do connecting flights from Chicago Midway Airport to Houston pass through?

    One-stop flights from Chicago Midway Airport to Houston most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 88% of one-stop connections
    • Dallas Love Field (DAL) - 4% of one-stop connections
    • Detroit Metropolitan Wayne County (DTW) - 4% of one-stop connections
    • Orlando (MCO) - 4% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Houston?

    Yes. Being flexible with your travel dates can save you up to 28% on the Chicago Midway Airport to Houston route. Monday is the cheapest departure day at $252 round-trip on average, while Sunday is the most expensive at $348, a difference of $96. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • At what point is a flight considered delayed from Chicago Midway Airport to Houston?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to Houston route, 20% of flights were delayed in the past 3 months, with delays averaging 1 hour 53 minutes.

  • How are flight departures from Chicago Midway Airport to Houston spread across the day?

    Morning is the busiest departure period on Chicago Midway Airport to Houston flights, with 50% of flights leaving in that window. Afternoon departures account for 25%, evening flights for 25%, and night flights for 0%.

  • What popular places can I visit in Houston?

    Some of the most popular sights in Houston are Downtown Houston, George R. Brown Convention Center and Galleria Mall. These are among the most viewed places in Houston on KAYAK.

  • What are the earliest and latest flights from Chicago Midway Airport to Houston?

    These are the earliest and latest flight times available from Chicago Midway Airport to Houston:

    • Earliest: departs at 5:05 am and lands at 7:42 am
    • Latest: departs at 11:05 pm and lands at 1:42 am.

    The flight takes about 2h 37m.

  • How expensive are last-minute Chicago Midway Airport to Houston flights?

    Last-minute fares on this route - booked within 2 weeks of departure - run 13% above the route average of $278. Book 19 weeks before departure for the lowest fares.

  • How long is a flight from Chicago Midway Airport to Houston?

    A nonstop flight from Chicago Midway Airport to Houston takes 2h 37m, covering 933 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Houston?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • How are flight prices from Chicago Midway Airport to Houston looking right now?

    One-way fares from Chicago Midway Airport to Houston are currently lower than usual. Average one-way flight prices are about $154, which is 12% below the typical average for this route.

  • How does Southwest’s on-time performance compare to other airlines on Chicago Midway Airport to Houston flights?

    Southwest is the only airline operating Chicago Midway Airport to Houston flights. 80% of its flights are on time.

  • How do delay rates compare for morning and evening flights from Chicago Midway Airport to Houston?

    Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

  • How much time can I save by choosing a different layover airport from Chicago Midway Airport to Houston?

    Flying via Dallas Love Field (DAL) gives the shortest average 1-stop total travel time at 4h 37m, compared with 6h 03m via Detroit Metropolitan Wayne County (DTW) and 7h 41m via Atlanta Hartsfield-Jackson (ATL).

  • What car rental options are available in Houston?

    Since Houston is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Houston George Bush Intcntl Airport (IAH) — daily rates from around $3:

    • ACO Rent A Car
    • Easirent
    • America Car Rental
    • Hertz
    • Thrifty

    Near Houston Hobby Airport (HOU) — daily rates from around $20:

    • Thrifty
    • Dollar
    • Alamo
    • Hertz
    • Budget

  • How much should I expect to pay for a Chicago Midway Airport to Houston flight?

    Round-trip flights from Chicago Midway Airport to Houston range from $178 to $406, with an average of $278 over the past 12 months. Anything below $178 counts as a good deal.

  • Which airlines offer Wi-Fi on Chicago Midway Airport to Houston flights?

    JetBlue is the only airline on the Chicago Midway Airport to Houston route offering in-flight Wi-Fi. Pricing depends on fare class.

Your guide to booking Chicago Midway Airport to Houston flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Monday departure instead of Sunday. On this route, Monday flights average $252 - about $96 less than Sunday (28% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 19 weeks before you fly. On this route, that window historically saves about 27% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Houston trip for February. Fares historically average $188 round-trip in that month - typically $194 less than the most expensive month, which is June (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Orlando Airport (MCO) can be cheaper than flying direct. The cheapest layover option averages $240 round-trip on this route - about $40 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, hotels close to the airport you're flying into can be a convenient option.

    Near Houston George Bush Intcntl Airport

    · Houston Airport Marriott at George Bush Intercontinental

    Near Houston Hobby Airport

    · DoubleTree by Hilton Hotel Houston Hobby Airport
    · Best Western Plus Hobby Airport Inn & Suites
    · TownePlace Suites by Marriott Houston Hobby Airport

Prefer to fly direct from Chicago Midway Airport to Houston?

 
Find which airlines fly direct from Chicago Midway Airport to Houston, which days they fly and book direct flights.

Direct departures

Chicago Midway to Houston

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Houston to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

More options for your flight from Midway to Houston

Complete your trip to Houston with a hotel stay or car rental

Car rentals in Houston
Hotels in Houston
Vacations in Houston