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Find cheap flights from Houston to Chicago Midway Airport from $44

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Houston to Midway departing on 6/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 6/1
Sat 6/8

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,740,974 times on KAYAK, and here is why:

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Cheap flight deals from Houston to Midway

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Houston to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:52 am - 1:21 pmIAH-MDW
2h 29mnonstop
7:35 am - 10:17 amMDW-IAH
2h 42mnonstop
$58Frontier
Find Deal
Sat, May 18 - Tue, May 21
10:52 am - 1:21 pmIAH-MDW
2h 29mnonstop
7:35 am - 10:17 amMDW-IAH
2h 42mnonstop
$64Frontier
Find Deal
Sat, May 18 - Tue, May 21
10:52 am - 1:21 pmIAH-MDW
2h 29mnonstop
7:35 am - 10:17 amMDW-IAH
2h 42mnonstop
$67Frontier
Find Deal
Sat, Jun 1 - Tue, Jun 4
10:52 am - 1:21 pmIAH-MDW
2h 29mnonstop
7:35 am - 10:17 amMDW-IAH
2h 42mnonstop
$68Frontier
Find Deal
Sat, Jun 1 - Tue, Jun 4
11:30 am - 5:03 pmIAH-MDW
5h 33m1 stop
10:11 am - 2:52 pmMDW-IAH
4h 41m1 stop
$202Delta
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Wed, Aug 28 - Sun, Sep 1
4:40 pm - 7:05 pmHOU-MDW
2h 25mnonstop
1:30 pm - 4:10 pmMDW-HOU
2h 40mnonstop
$322Southwest
Find Deal
Tue, Oct 1 - Thu, Oct 3
10:24 am - 3:50 pmHOU-MDW
5h 26m1 stop
6:00 am - 12:22 pmMDW-HOU
6h 22m1 stop
$323Delta
Find Deal
Wed, May 15 - Sat, May 18
9:40 am - 12:20 pmHOU-MDW
2h 40mnonstop
8:25 am - 1:05 pmMDW-HOU
4h 40m1 stop
$327Southwest
Find Deal
Tue, Oct 1 - Thu, Oct 3
9:30 am - 1:25 pmHOU-MDW
3h 55m1 stop
8:25 am - 1:05 pmMDW-HOU
4h 40m1 stop
$336Southwest
Find Deal
Tue, Oct 1 - Thu, Oct 3
1:04 pm - 5:59 pmHOU-MDW
4h 55m1 stop
1:05 pm - 6:21 pmMDW-HOU
5h 16m1 stop
$396Delta
Find Deal
Wed, Jul 31 - Wed, Aug 7

Flights from Houston to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Houston to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Houston to Chicago Midway Airport flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Houston to Chicago Midway Airport.
Our data shows that the cheapest route for a one-way flight from Houston to Chicago Midway Airport cost $29 and was between Houston George Bush Intcntl Airport and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $52.

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

The average price of all flights from Houston to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Houston to Chicago Midway Airport. For your return ticket, we recommend flying on a Tuesday and avoiding Wednesdays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Houston to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Houston to Chicago Midway Airport is March, where tickets cost $145 on average. On the other hand, the most expensive months are December and July, where the average cost of tickets is $378 and $364 respectively.

Which airlines provide the cheapest flights from Houston to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($44) and Delta ($104). The cheapest round-trip tickets were found on Frontier ($58) and Delta ($202).

Which airlines fly non-stop between Houston and Chicago Midway Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Houston to Chicago Midway Airport.
There are 2 airlines that fly nonstop from Houston to Chicago Midway Airport. They are Frontier and Southwest. The cheapest airline for this route is Frontier, with the best one-way deal found costing $60. On average, the best prices for this route can be found at Frontier.

How many flights are there between Houston and Chicago Midway Airport per day?

Each day, there are between 7 and 10 nonstop flights that take off from Houston and land in Chicago Midway Airport, with an average flight time of 2h 27m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 58 flights. The most frequent day of departure is Tuesday, when 17% of all weekly flights depart. The fewest flights depart on a Friday.

Which cabin class options are there for flights between Houston and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Houston to Chicago Midway Airport take?

There are no direct flights from Houston to Chicago Midway Airport. The quickest journey takes 2h 20m.

Good to know

Cheapest flight

$44
Flight from Houston George Bush Airport to Chicago Midway Airport

When to book flights from Houston to Midway

Are your dates flexible? Find out the best times to travel from Houston to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Houston to Chicago Midway Airport flights

  • What is the cheapest flight from Houston to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Houston to Chicago Midway Airport was $44 for a one-way ticket and $58 for a round-trip.

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

    Yes, you'll most likely have to show a valid passport before boarding the plane in Houston and on arrival in Chicago Midway Airport.

  • Which airports will I be using when flying from Houston to Chicago Midway Airport?

    On your way to Chicago Midway Airport, you’ll fly out from one of these Houston airports: Houston Hobby or Houston George Bush Intcntl. You’ll be landing at Chicago Midway.

  • Which aircraft models fly most regularly from Houston to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Houston to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Houston and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Houston to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Houston to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Houston to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Houston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Houston to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Houston with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Houston to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Houston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Houston to Chicago Midway Airport?

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

Nonstop departures

Houston to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Southwest

Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Nonstop returns

Chicago Midway to Houston

Monday

Southwest

Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Southwest

Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights
See more direct flights

Book cheap flights from Houston to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Houston to Chicago found on KAYAK in the last 72 hours.
6/4Tue
nonstopFrontier
2h 29mIAH-MDW
$44
6/1Sat
nonstopFrontier
2h 29mIAH-MDW
$48
5/11Sat
nonstopFrontier
2h 27mIAH-MDW
$49
7/20Sat
1 stopDelta
5h 34mIAH-MDW
$104
5/15Wed
2 stops
13h 18mIAH-MDW
$112
5/31Fri
1 stopAllegiant Air
5h 27mHOU-MDW
$127
5/15Wed
3 stops
38h 34mIAH-MDW
$132
6/3Mon
1 stopAllegiant Air
5h 27mHOU-MDW
$152
5/11Sat
1 stopDelta
4h 31mHOU-MDW
$154
5/14Tue
1 stopVolaris
11h 23mIAH-MDW
$324

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Last minute flights from Houston to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Houston to Chicago that are departing in the next 10 days.
5/7Tue
nonstopFrontier
2h 27mIAH-MDW
5/14Tue
nonstopFrontier
2h 48mMDW-IAH
$99
5/7Tue
nonstopFrontier
2h 27mIAH-MDW
5/9Thu
multi-stopFrontier
9h 08mMDW-IAH
$123
5/7Tue
nonstopFrontier
2h 27mIAH-MDW
5/14Tue
multi-stopFrontier
9h 48mMDW-IAH
$130
5/7Tue
nonstopFrontier
2h 27mIAH-MDW
5/9Thu
nonstopFrontier
2h 48mMDW-IAH
$136
5/5Sun
nonstopSouthwest
2h 20mIAH-MDW
5/9Thu
nonstopSouthwest
2h 40mMDW-IAH
$498
5/5Sun
multi-stopSouthwest
5h 25mIAH-MDW
5/9Thu
nonstopSouthwest
2h 40mMDW-IAH
$507
5/4Sat
multi-stopDelta
6h 37mHOU-MDW
5/8Wed
multi-stopDelta
6h 22mMDW-HOU
$628
5/5Sun
multi-stopDelta
6h 37mHOU-MDW
5/7Tue
multi-stopDelta
5h 42mMDW-HOU
$657
5/7Tue
multi-stop
11h 23mIAH-MDW
5/12Sun
multi-stop
19h 01mMDW-IAH
$723
5/7Tue
multi-stopVolaris
11h 23mIAH-MDW
5/14Tue
multi-stopVolaris
22h 15mMDW-IAH
$777

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Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Houston

Cabin classes:

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