MDW - HOU

$79 Find Cheap Flights from Chicago Midway Airport to Houston Hobby Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Hobby departing on 3/7. 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
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Houston Hobby Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Houston, 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 Chicago to Houston, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$157
Overall average: $218
Southwest
Sat 2/21Sat 2/28
MDW - HOU • Non-stop
Cheapest non-stop
$157
Typical prices: $158-$282
Southwest
Sat 2/21Wed 2/25
MDW - HOU • Non-stop
Top airlines
Southwest
Cheapest • from $157 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 11% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 52% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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 Hobby!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Hobby (MDW-HOU)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Hobby 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Hobby

Sat, Feb 21 - Sat, Feb 28
Southwest Logo
8:55 pm - 11:45 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
6:55 pm - 9:20 pm
HOU
-
MDW
2h 25mnonstop
$157Southwest
Sat, Mar 7 - Tue, Mar 10
Southwest Logo
6:50 pm - 9:40 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
9:30 pm - 11:55 pm
HOU
-
MDW
2h 25mnonstop
$174Southwest
Tue, Feb 17 - Tue, Feb 24
Southwest Logo
5:55 am - 8:50 am
MDW
-
HOU
2h 55mnonstop
Southwest Logo
8:30 pm - 10:55 pm
HOU
-
MDW
2h 25mnonstop
$177Southwest
Sat, Feb 21 - Wed, Feb 25
Southwest Logo
8:55 pm - 11:45 pm
MDW
-
HOU
2h 50mnonstop
Southwest Logo
4:30 pm - 8:40 pm
HOU
-
MDW
4h 10m
1 stop
$187Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
10:15 am - 1:00 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
6:10 pm - 8:35 pm
HOU
-
MDW
2h 25mnonstop
$191Southwest
Mon, Feb 23 - Fri, Feb 27
Southwest Logo
8:30 pm - 11:15 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
8:45 pm - 11:10 pm
HOU
-
MDW
2h 25mnonstop
$197Southwest
Tue, Mar 10 - Wed, Mar 11
Southwest Logo
9:05 pm - 11:50 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
7:30 am - 12:00 pm
HOU
-
MDW
4h 30m
1 stop
$198Southwest
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
1:20 pm - 5:50 pm
MDW
-
HOU
4h 30m
1 stop
Southwest Logo
8:30 pm - 10:55 pm
HOU
-
MDW
2h 25mnonstop
$203Southwest
Tue, Mar 31 - Tue, Mar 31
Southwest Logo
2:10 pm - 4:55 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
9:30 pm - 11:55 pm
HOU
-
MDW
2h 25mnonstop
$205Southwest
Mon, Mar 9 - Wed, Mar 11
Delta Logo
5:40 pm - 10:42 pm
MDW
-
HOU
5h 02m
1 stop
Delta Logo
6:00 am - 12:02 pm
HOU
-
MDW
6h 02m
1 stop
$207Delta
Booking Insights

KAYAK's insights & trends for Midway to Hobby flights

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

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

The average price of all round-trip flights from Chicago Midway Airport to Houston Hobby Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Houston Hobby Airport on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to Houston Hobby Airport. For your return ticket, we recommend flying on a Monday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Houston Hobby 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 Chicago Midway Airport to Houston Hobby Airport is September, where tickets cost $125 (return) on average. On the other hand, the most expensive months are July and December, where the average cost of round-trip tickets is $335 and $318 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Houston Hobby Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Houston Hobby Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to Houston Hobby Airport, you should book around 2 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$79
Best time to beat the crowds with an average 52% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Chicago Midway Airport to Houston Hobby Airport

When to book flights from Midway to Hobby

Are your dates flexible? Find out the best times to travel from Midway to Hobby 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 Chicago Midway Airport to Houston Hobby Airport flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Houston Hobby Airport was $79 for a one-way ticket and $157 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

    Chicago Midway Airport and Houston Hobby Airport are both served by 1 main airport. You will leave Chicago Midway Airport from Chicago Midway and will be arriving at Houston Hobby.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Houston Hobby Airport?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Chicago Midway Airport to Houston Hobby Airport flight route.

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

    The Airbus A321neo is the aircraft model that flies most regularly on the Chicago Midway Airport to Houston Hobby Airport flight route.

  • On which days can I fly direct from Chicago Midway Airport to Houston Hobby Airport?

    There are nonstop flights from Chicago Midway Airport to Houston Hobby Airport on a daily basis.

  • Which is the best airline for flights from Chicago to Houston, Southwest or Spirit Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Houston are Southwest and Spirit Airlines. With an average price for the route of $329 and an overall rating of 8.0, Southwest is the most popular choice. Spirit Airlines is also a great choice for the route, with an average price of $195 and an overall rating of 6.3.

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Houston Hobby Airport from Chicago Midway Airport 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 Chicago Midway Airport to Houston Hobby 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 Houston Hobby Airport with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and HOU can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Houston Hobby 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 Houston Hobby Airport from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Houston Hobby Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $210 or less one-way and $238 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Houston Hobby Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Houston Hobby.
Find which airlines fly direct from Chicago Midway Airport to Houston Hobby Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Houston Hobby

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 Hobby 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

Reviews of the top 3 airlines serving from Midway to Hobby

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Houston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Hobby? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4267 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

Great flight but super high price. Glad it was a business trip and not personal

10.0 ExcellentPieter, Jan 2026
LGB - DAL
Read more Southwest reviews

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

No delays and arrived to destination 30 min early. Staff was super friendly.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Spirit Airlines has a reputation for being a terrible, cheap airline, this is why. I took a gamble on them, having never flown with them before, and the flight got cancelled. First they delayed the flight about 4 times before finally canceling it because a flight attendant didn’t show up to work that day. That’s so stupid. When I asked a ticketing agent she said that’s “company policy”. A company policy that inconveniences hundreds of passengers because a single flight attendant didn’t show is ridiculous and inefficient. I will never, ever try flying Spirit Airlines again.

Cancelled my flight and the earliest that they are willing give me for the next flight which was 3 days later on a weekday. Only accommodation they are willing to give was $30 airline credit that will expire in 1 year

Flight was canceled, huge lines to get baggage returned. Most other airlines had delays but not widespread cancellations like Spirit.

My baby was crying uncontrollably for the longest time and the entire crew was SO supportive, I’m so appreciative of them. Thank you so much for the support during an exhausting moment. We got very lucky.

Uncomfortable seats and tiny tray table. Expensive snacks. Flight was on time and crew was pleasant but take me back to Southwest!

I didn't order food. I requested a Tomato juice and was given a boody mary mix. The serve needs to warn the customer what their given. It wasn't a huge deal, but I wasted $4.50.

EVERYTHING! It was so bad that I will be filing a claim for reimbursement for my seat as I could not fully sit in it due to an obese person being next to me and spilling over into my "space." And my personal item in the overhead been got crushed between two suitcases, so now my business laptop has been damaged beyond repair. Also, it was expensive! Since you pay for EVERYTHING, the cost of the trip was probably more than if you I used an airline that was not discounted. I will NEVER fly Spirit Airlines again!

One of worst experienc my family have every had with this airline. I was informed my Kayak that my flight was delayed and that my family will not make it to houston for our connecting flight. I contacted Spirit customer service to get my family on a later flight due to the delay in Vagas and them not making their connecting flight. The customer rep keep telling me that the flight from vagas is on time and not delayed. She even make to go to the spirit app on my phone and show me how to look up weather or not the flight was delayed. The app showed "on time" 20 minutes later when my family arrived at the airport for their flight, they were told that the flight was delayed and she will not make her connecting flight. I call spirit airline customer support again that night and spoke to another rep who apologize for his collegue and he told me that my family will receive a credit for this, this was on Saturday I still have not received the credit or an email letting me know when I will be credited for this inconvenience. This is not good business and it need to be fixed.

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Everything you need to know for your flight from Midway to Hobby

Information on your arrival and departure airports