HOU - CHI

$95 Find Cheap Flights from Houston Hobby Airport to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hobby to Chicago departing on 8/19. 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

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Everything you should know

Cheapest round-trip
$179
Typical prices: $212-$372
Southwest
Mon 8/17Thu 8/20
HOU - MDW • Non-stop
Cheapest one-way
$95
Typical prices: $178-$259
Southwest
Wed 8/19
HOU - MDW • 1 stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 25m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top routes
HOU
-
MDW
Cheapest
HOU
-
MDW
Most popular
Insights
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Avoid delays
Southwest
Most punctual • 79% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
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Insights
Top layover airports
Raleigh (RDU)
Cheapest • Avg $197 (round-trip)
Dallas (DFW)
Shortest trip • 4h 55m (one-way)
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 33% compared to booking last minute.
Insights
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Insights
When to travel
February
Cheapest • 90% price drop
July
Most popular
Good to know
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hobby to Chicago (HOU-CHI)

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

Mon, Aug 17 - Thu, Aug 20
Southwest Logo
5:00 am - 7:25 am
HOU
-
MDW
2h 25mnonstop
Southwest Logo
7:25 am - 9:55 am
MDW
-
HOU
2h 30mnonstop
$179Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
7:55 pm - 10:15 pm
HOU
-
MDW
2h 20mnonstop
Southwest Logo
5:25 am - 7:50 am
MDW
-
HOU
2h 25mnonstop
$180Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
7:55 pm - 10:15 pm
HOU
-
MDW
2h 20mnonstop
Southwest Logo
1:05 pm - 6:25 pm
MDW
-
HOU
5h 20m
1 stop
$185Southwest
Wed, Aug 5 - Thu, Aug 13
Southwest Logo
11:55 am - 4:20 pm
HOU
-
MDW
4h 25m
1 stop
Southwest Logo
5:30 pm - 8:00 pm
MDW
-
HOU
2h 30mnonstop
$189Southwest
Sat, Aug 8 - Tue, Aug 11
Southwest Logo
8:40 am - 1:40 pm
HOU
-
MDW
5h 00m
1 stop
Southwest Logo
7:50 am - 10:25 am
MDW
-
HOU
2h 35mnonstop
$190Southwest
Sat, Aug 22 - Tue, Aug 25
Southwest Logo
10:25 am - 2:15 pm
HOU
-
MDW
3h 50m
1 stop
Southwest Logo
10:10 am - 2:00 pm
MDW
-
HOU
3h 50m
1 stop
$191Southwest
Tue, Aug 11 - Thu, Aug 13
Southwest Logo
11:25 am - 4:55 pm
HOU
-
MDW
5h 30m
2 stops
Southwest Logo
7:25 am - 9:55 am
MDW
-
HOU
2h 30mnonstop
$194Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
6:00 pm - 11:20 pm
HOU
-
MDW
5h 20m
1 stop
Southwest Logo
1:05 pm - 6:25 pm
MDW
-
HOU
5h 20m
1 stop
$195Southwest
Tue, Aug 4 - Tue, Aug 11
Delta Logo
6:00 am - 11:51 am
HOU
-
MDW
5h 51m
1 stop
Delta Logo
5:10 pm - 10:05 pm
MDW
-
HOU
4h 55m
1 stop
$199Delta
Tue, Aug 4 - Wed, Aug 5
Delta Logo
5:20 pm - 11:57 pm
HOU
-
ORD
6h 37m
1 stop
Delta Logo
6:40 am - 12:16 pm
ORD
-
HOU
5h 36m
1 stop
$199Delta
Booking Insights

KAYAK's insights & trends for Hobby to Chicago flights

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

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

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

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

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

The cheapest return flight from Houston Hobby Airport to Chicago costs $209 on the route between Houston Hobby Airport (HOU) and Chicago Midway Airport (MDW). It is also the most popular route.

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

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

Your flight ticket price will generally be cheaper if you fly to Chicago on a Friday and more expensive on a Sunday. On your return trip to Houston Hobby Airport, you should consider flying back on a Thursday, and avoid Mondays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Houston Hobby Airport to Chicago, 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 Hobby Airport to Chicago is February, where tickets cost $29 (return) on average. On the other hand, the most expensive months are August and October, where the average cost of round-trip tickets is $589 and $546 respectively.

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

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 $384 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Houston Hobby Airport to Chicago, 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 Houston Hobby Airport to Chicago, you should book around 4 weeks before departure, which saves you about 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$95
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Houston Hobby Airport to Chicago Midway Airport

When to book flights from Hobby to Chicago

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

  • Do Chicago airports have accommodation?

    Travelers can relax and unwind at some of the luxury hotels located within Midway Airport, like Residence Inn Midway Airport hotel located just 1 mile away from the terminal. You can stay at the Hilton O'Hare Airport Hotel right across T1, T2, and T3.

  • Does Houston Hobby Airport have services for passengers with limited mobility?

    Those with limited mobility can receive baggage and wheelchair assistance from Skycap Service. The airport also has wheelchair-accessible restrooms and elevators. Those with disabilities should communicate any other assistance they may require through the airline before their departure date.

  • What family-friendly facilities do Chicago airports have?

    There is a nursing room on Concourse C at Midway Airport. Most restrooms at Midway Airport have baby-changing stations. You will also find kid-friendly restaurants at the airport. There is a kids'play area in Terminal 2 of O'Hare Airport. Nursing rooms are also available at Terminals 1 to 5.

  • Does Hobby Airport have affordable parking options?

    An affordable parking lot at Hobby Airport is the Ecopark, where you can leave your car for a fee of around $9. Another option is the Terminal Parking garage, which charges around $13 for the daily parking option. Valet parking is also available for around $28 per day.

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

    In the last 5 days, the lowest price for a flight from Houston Hobby Airport to Chicago was $95 for a one-way ticket and $179 for a round-trip.

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

    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 Houston Hobby Airport to Chicago?

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

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

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

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

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

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are Southwest and Delta. With an average price for the route of $324 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $321 and an overall rating of 7.8.

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

    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 Hobby Airport to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Houston Hobby 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 Houston Hobby Airport to Chicago?

    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 with an airline and back to Houston Hobby Airport with another airline.

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

    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 from Houston Hobby 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 Houston Hobby Airport to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $211 or less one-way and $349 or less round-trip.
  • If you intend to fly from Houston's Hobby Airport (HOU) to Chicago's Midway Airport (MDW) without having layovers during the trip, you can get a flight operated by Southwest Airlines. If you do not mind a layover, you can use Delta Air Lines.
  • If you’re looking for a convenient transportation means from Downtown Houston to Hobby Airport, you should book the airport shuttles, which charge a minimum fare of around $19. The shuttles will drop you off outside the baggage claim. The cheaper alternative is the 73 Bellfort Metro, which charges around $1.25.
  • Several amenities at Chicago Midway Airport make traveling through the airport easier for those with limited mobility. Elevators have raised letters and braille, family assisted care restrooms, wheelchair-accessible telephone booths, and wheelchair escorts.
  • Exploring the vibrant Chicago city in a rental car will not only be convenient but will give you maximum flexibility. Midway Airport has several car rentals, like Enterprise, located on Level 2 of the airport's parking garage. The Avis desk is located on Level 3.
  • If you have plenty of time to kill before your flight, you can explore some of Hobby Airport's famous attractions, like the museum located at the airport's terminal, or marvel at the art deco design, which reflects Houston's Aviation era.
  • If you fly in from Houston, landing at Chicago Midway Airport provides more convenience than landing at the bustling O'Hare Airport (ORD). Because Midway is relatively smaller, you can expect shorter lines and faster service. Midway Airport is also closer to Downtown Chicago than O'Hare Airport.
  • From Chicago O'Hare Airport, you can board the Blue Line L train, which takes around 45min to reach Downtown Chicago. You can find the L Train, which charges a minimum rate of approximately $5 at either Terminal 1, Terminal 2, or Terminal 3.

Prefer to fly direct from Houston Hobby Airport to Chicago?

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

Direct departures

Houston Hobby to Chicago

Monday

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Tuesday

Southwest

Southwest

Wednesday

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Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago to Houston Hobby

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

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Southwest

Thursday

Southwest

Southwest

Friday

Southwest

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Saturday

Southwest

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Sunday

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See more direct flights

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

Information on your arrival and departure airports

Houston Hobby Airport (HOU)