CHI - HOU

$79 Find Cheap Flights from Chicago 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 Chicago to Hobby departing on 4/21. 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
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Everything you should know

Cheapest round-trip
$157
Overall average: $275
Southwest
Wed 4/15Tue 4/21
MDW - HOU • Non-stop
Cheapest one-way
$79
Typical prices: $89-$160
Southwest
Tue 4/21
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
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 50m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
MDW
-
HOU
Cheapest
MDW
-
HOU
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Southwest
Most punctual • 82% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 19% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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We hope you love your trip to Hobby!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Hobby (CHI-HOU)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago 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 Chicago to Hobby

Wed, Apr 15 - Tue, Apr 21
Southwest Logo
7:25 am - 10:05 am
MDW
-
HOU
2h 40mnonstop
Southwest Logo
8:40 pm - 11:05 pm
HOU
-
MDW
2h 25mnonstop
$157Southwest
Tue, Apr 7 - Sat, Apr 25
Southwest Logo
7:25 am - 10:05 am
MDW
-
HOU
2h 40mnonstop
Southwest Logo
3:25 pm - 5:50 pm
HOU
-
MDW
2h 25mnonstop
$169Southwest
Fri, May 1 - Tue, May 5
Southwest Logo
9:40 pm - 12:20 am
MDW
-
HOU
2h 40mnonstop
Southwest Logo
6:10 pm - 8:35 pm
HOU
-
MDW
2h 25mnonstop
$177Southwest
Thu, Apr 16 - Sun, Apr 19
Southwest Logo
9:40 pm - 12:20 am
MDW
-
HOU
2h 40mnonstop
Southwest Logo
5:00 am - 7:25 am
HOU
-
MDW
2h 25mnonstop
$181Southwest
Tue, Mar 17 - Tue, Mar 24
Southwest Logo
2:10 pm - 4:55 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
9:30 pm - 11:55 pm
HOU
-
MDW
2h 25mnonstop
$191Southwest
Sat, Apr 25 - Sun, May 3
Southwest Logo
6:05 pm - 8:50 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
5:00 am - 7:25 am
HOU
-
MDW
2h 25mnonstop
$194Southwest
Sat, Apr 18 - Sat, Apr 25
Delta Logo
9:48 am - 4:28 pm
ORD
-
HOU
6h 40m
1 stop
Delta Logo
6:00 am - 1:14 pm
HOU
-
ORD
7h 14m
1 stop
$197Delta
Sat, Apr 18 - Sat, Apr 25
Delta Logo
5:21 pm - 11:08 pm
MDW
-
HOU
5h 47m
1 stop
Delta Logo
10:48 am - 4:29 pm
HOU
-
MDW
5h 41m
1 stop
$197Delta
Sat, Apr 18 - Mon, Apr 27
Delta Logo
9:48 am - 4:28 pm
ORD
-
HOU
6h 40m
1 stop
Delta Logo
5:23 pm - 11:59 pm
HOU
-
ORD
6h 36m
1 stop
$199Delta
Wed, Mar 25 - Thu, Mar 26
Southwest Logo
5:35 pm - 8:20 pm
MDW
-
HOU
2h 45mnonstop
Southwest Logo
5:05 am - 7:25 am
HOU
-
MDW
2h 20mnonstop
$199Southwest
Booking Insights

KAYAK's insights & trends for Chicago to Hobby flights

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

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Houston Hobby Airport departing in April.

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Houston Hobby Airport costs $224 on the route between Chicago Midway Airport (MDW) and Houston Hobby Airport (HOU). It is also the most popular route.

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

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

For Chicago to Houston Hobby Airport, Thursday is the cheapest day to fly on average and Monday is the most expensive. Flying from Houston Hobby Airport back to Chicago, the best deals are generally found on Friday, with Monday being the most expensive.

What is the cheapest month to fly from Chicago 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 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 to Houston Hobby Airport is September, where tickets cost $177 (return) on average. On the other hand, the most expensive months are March and May, where the average cost of round-trip tickets is $256 and $245 respectively.

Can I save money by flying with a layover from Chicago to Houston Hobby Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $270 on average.

How far in advance should I book a flight from Chicago 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 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 to Houston Hobby Airport, you should book around 3 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$79
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago Midway Airport to Houston Hobby Airport

When to book flights from Chicago to Hobby

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

  • Which accommodation options are available at Hobby Airport?

    Located 1 mile away from the airport are luxurious hotels like the Days Inn & Suites, the DoubleTree by Hilton, Hampton Inn, and Holiday Inn, which provide cozy accommodations. The hotels also offer complimentary shuttles.

  • Does O'Hare Airport have disabled-friendly amenities?

    O'Hare Airport accommodates the needs of those with special needs and disabilities by providing amenities like elevators, Braille, accessible parking spots at lots B, C, D, F. G, H with ramps and elevators close by, operator-assisted phones in T2, T3, and T5, and mobility assistance.

  • What kind of public transportation can I use to get to Midway Airport from downtown Chicago?

    There is a regular and affordable train service—the Orange Line—that transports travelers from Downtown Chicago to MDW. Orange-Line trains take between 20min and 25min to complete the journey and charge around $2.50.

  • Does Midway Airport have lounges?

    Midway Airport has only one lounge, the USO lounge in Concourse C, which is open to those actively serving in the military and their families free of charge. The cozy lounge is equipped with gaming stations, a kitchenette with complimentary refreshments, TVs, and reading materials.

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

    In the last 3 days, the lowest price for a flight from Chicago 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 and Houston Hobby Airport?

    A passport is not required to fly from Chicago to Houston Hobby Airport.

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

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Houston Hobby.

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

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

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

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

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

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Houston Hobby Airport, with oneworld being the most commonly used for this route.

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Houston are Southwest and United Airlines. With an average price for the route of $311 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $326 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Chicago 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 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 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 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 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 with another airline.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $198 or less one-way and $313 or less round-trip.
  • Travelers can get nonstop flights to Hobby Airport (HOU) from Midway Airport (MDW) with Southwest Airlines. O'Hare Airport (ORD), which serves as a hub for United and American Airlines, also operates nonstop flights to Hobby Airport through both airlines.
  • O'Hare Airport provides tranquil spaces in their sophisticated lounges to ensure travelers get some much-needed relaxation time before their flights. The United Airlines United Club, located in Terminal 2, is one such lounge that one can access by paying around $59.
  • If you choose to drive yourself to Midway Airport, you can leave your vehicle at one of the long-term parking lots. The economy lot, which you will find on the northwest side of the terminal, provides convenient and affordable long-term parking at a rate of about $15. Free shuttles are available from the parking lot.
  • Hobby Airport provides families with essential amenities to ensure they have a stress-free time while at the airport. There is a children's play area in the west concourse. The airport also has two mothers'rooms situated right next to Gate 46 and Gate 4.
  • Travelers arriving at Hobby Airport can find Metro bus 40, which stops right outside the arrivals area. The Metro bus takes approximately 60min to travel from Hobby Airport to downtown Houston. The standard fare for the one-way trip is around $1.25.
  • Midway Airport has plenty of paintings, exhibits, sculptures, and murals spread all over the airport to give travelers a one-of-a-kind traveling experience. On the Mezzanine level of Midway Airport is the hanging sculpture that poetically links human-made and natural aviation.
  • Taking the GO Airport shuttle is a convenient way to travel from O'Hare Airport to downtown Chicago. Only passengers with one suitcase of standard size and one hand luggage are allowed onboard the shuttle. The standard fare for the shuttle trip, which takes approximately 45min, is around $30.

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

Direct departures

Chicago 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

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 5 airlines serving from Chicago 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 Chicago 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 4298 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

4.0 Okaybyron, Feb 2026
DAL - SAT
Read more Southwest reviews

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

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.

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Very old flight - time to retire it for newer airplanes

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Everything except the food and entertainment. It was a great experience though

Delayed, toilets did not flush, pilot parked to far away from Gate

Check-in, boarding and the flight from Phoenix to Houston was quick and easy. The flight from Houston to Shreveport was delayed 5 hours. It was frustrating but I think United handled it the best they could.

The staff was hospitable and professional. The seat had a bit of wear. The winner shade was stuck 1/4 open. I received the best of both worlds. The morning sun was able to come in and blind the screen i was trying to use while at the same time it was too low to look out and enjoy the view. Rather embarrassing for a 1st class ticket.

United is an incompetent airline. They parked the plane on the tarmac for an hour after arriving because they “didn’t have a gate available” it was actually some sort of lie because as we de planed there were approximately 9 open and manned and empty gates that we walked past. Many people on the flight missed connections for the hour long sit on the tarmac. Utterly baffling and incompetent behavior from United flight ops.

I boarded flight UA#1318 at Sacramento International Airport going back to Houston TX. The flight was scheduled at 5:10am. I was able to check in virtually using the United Airlines app. When I entered the airport, there was no one outside assisting with checked bags as it was for Delta Airlines. Immediately upon entering, there was a LONG, EXTREMELY LONG line to the kiosks to get boarding passes. I stand in line to get boarding passes then had to move to ANOTHER EXTREMELY LONG line to get my bags checked in. While standing in this line, we noticed an agent taking customers to 3 at a time to her station to check their bags in. Lucky for me, she called me back, checked my bags for me and I was on my way. I then encountered another long line at the TSA check and to avoid I ending up having to sign up for CLEAR to bypass it. So glad, I did.,...Both of my flights were great with no issues, butthe check in progress at Bush Airport was so much smoother. Check-in at SMF airport needs to be anaylzed and corrected. Do better United, I know you can....thanks

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

Flight was delayed for 12 h. They should stop overlooking flights.

All of our flights were canceled, though every other airline was flying out and in

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!

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

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.

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

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