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Flights from Houston to Chicago – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

HOU to MDW flights and routes map HOU to MDW – All flight route options from William P. Hobby Airport, Texas, USA to Chicago Midway International, Illinois, USA. These flights are operated by 2 airlines. Fly non-stop with Southwest Airlines or choose from 21 different transit flights. The shortest flight time is 2 hours and 25 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA HOU William P. Hobby Airport Houston, TX, USA
USA MDW Chicago Midway , IL, USA
HOU
William P. Hobby Airport
USAHouston, TX, USA
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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22 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 5-7 flights per day.

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2h 25m

Southwest Airlines
Non-stop with Southwest Airlines.
2h 25m
5-7 flights per day.
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1 stop route options with the same airline:

Duration

Via Oklahoma City OKC
1 stop with Southwest Airlines. 0-1 flights per day.
Tue,Wed & Sun

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4h 30m

Tue,Wed & Sun
Via Oklahoma City OKC
1 stop with Southwest Airlines.
4h 30m
0-1 flights per day.
Tue,Wed & Sun
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Via Tulsa TUL
1 stop with Southwest Airlines. 0-2 flights per day.
Begins in 31/8

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4h 40m

Begins in 31/8
Via Tulsa TUL
1 stop with Southwest Airlines.
4h 40m
0-2 flights per day.
Begins in 31/8
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Via Saint Louis STL
1 stop with Southwest Airlines. 1-3 flights per day.

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4h 50m

Via Saint Louis STL
1 stop with Southwest Airlines.
4h 50m
1-3 flights per day.
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Via Kansas City MCI
1 stop with Southwest Airlines. 1-3 flights per day.

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5h 00m

Via Kansas City MCI
1 stop with Southwest Airlines.
5h 00m
1-3 flights per day.
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Via Indianapolis IND
1 stop with Southwest Airlines.
Begins in 9/8

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5h 00m

Begins in 9/8
Via Indianapolis IND
1 stop with Southwest Airlines.
5h 00m
Begins in 9/8
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Via Columbus CMH
1 stop with Southwest Airlines. 0-1 flights per day.
Only saturdays

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5h 13m

Only saturdays
Via Columbus CMH
1 stop with Southwest Airlines.
5h 13m
0-1 flights per day.
Only saturdays
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Via Austin AUS
1 stop with Southwest Airlines. 1-3 flights per day.

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5h 20m

Via Austin AUS
1 stop with Southwest Airlines.
5h 20m
1-3 flights per day.
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Via New Orleans MSY
1 stop with Southwest Airlines. 1-3 flights per day.

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5h 20m

Via New Orleans MSY
1 stop with Southwest Airlines.
5h 20m
1-3 flights per day.
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Via Dallas DAL
1 stop with Southwest Airlines. 6-9 flights per day.

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5h 25m

Via Dallas DAL
1 stop with Southwest Airlines.
5h 25m
6-9 flights per day.
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Via Birmingham BHM
1 stop with Southwest Airlines. 0-1 flights per day.
Sat & Sun

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5h 30m

Sat & Sun
Via Birmingham BHM
1 stop with Southwest Airlines.
5h 30m
0-1 flights per day.
Sat & Sun
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Via Memphis MEM
1 stop with Southwest Airlines. 0-1 flights per day.
Begins in 10/8

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5h 33m

Begins in 10/8
Via Memphis MEM
1 stop with Southwest Airlines.
5h 33m
0-1 flights per day.
Begins in 10/8
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Via Louisville SDF
1 stop with Southwest Airlines. 0-1 flights per day.

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5h 40m

Via Louisville SDF
1 stop with Southwest Airlines.
5h 40m
0-1 flights per day.
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Via Atlanta ATL
1 stop with Southwest Airlines. 0-5 flights per day.

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5h 48m

Via Atlanta ATL
1 stop with Southwest Airlines.
5h 48m
0-5 flights per day.
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Via Pittsburgh PIT
1 stop with Southwest Airlines. 0-1 flights per day.

SHOW SCHEDULE
5h 50m

Via Pittsburgh PIT
1 stop with Southwest Airlines.
5h 50m
0-1 flights per day.
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Via Atlanta ATL
1 stop with Delta Air Lines. 2-4 flights per day.

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5h 55m

Via Atlanta ATL
1 stop with Delta Air Lines.
5h 55m
2-4 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines. 3-5 flights per day.

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6h 00m

Via Nashville BNA
1 stop with Southwest Airlines.
6h 00m
3-5 flights per day.
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Via San Antonio SAT
1 stop with Southwest Airlines. 0-1 flights per day.

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6h 00m

Via San Antonio SAT
1 stop with Southwest Airlines.
6h 00m
0-1 flights per day.
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Via Omaha OMA
1 stop with Southwest Airlines. 0-1 flights per day.
Tue,Wed & Sun

SHOW SCHEDULE
6h 15m

Tue,Wed & Sun
Via Omaha OMA
1 stop with Southwest Airlines.
6h 15m
0-1 flights per day.
Tue,Wed & Sun
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Via Savannah SAV
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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6h 40m

Only sundays
Via Savannah SAV
1 stop with Southwest Airlines.
6h 40m
0-1 flights per day.
Only sundays
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Via Minneapolis MSP
1 stop with Southwest Airlines. 0-1 flights per day.
Only sundays

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7h 15m

Only sundays
Via Minneapolis MSP
1 stop with Southwest Airlines.
7h 15m
0-1 flights per day.
Only sundays
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Via Midland MAF
1 stop with Southwest Airlines.
Begins in 31/8

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7h 50m

Begins in 31/8
Via Midland MAF
1 stop with Southwest Airlines.
7h 50m
Begins in 31/8
SHOW SCHEDULE
Via Charlotte CLT
1 stop with Southwest Airlines. 0-1 flights per day.
Mon,Thu & Fri

SHOW SCHEDULE
8h 30m

Mon,Thu & Fri
Via Charlotte CLT
1 stop with Southwest Airlines.
8h 30m
0-1 flights per day.
Mon,Thu & Fri
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Houston to Chicago flights

There are over 22 airlines and as many as 265 flights every week to this destination. You can fly non-stop to Chicago (MDW) from Houston (HOU) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Oklahoma City, Tulsa or any other of the 21 alternatives with connectiing airports.

Tip! You can also fly to Chicago from George Bush Intcntl Houston (IAH).

Houston to Chicago with Southwest Airlines

You can fly non-stop every weekday with flights departing from 5:00 am to 10:00 pm. You can also catch a transit flight via Oklahoma City or Tulsa.

With Delta Air Lines

If you fly from Houston with Delta Air Lines you will do a stopover in Atlanta, ATL before reaching Chicago. This flight trip will take 5 hours and 55 minutes and you can fly every weekday with departures between 6:00 am and 4:00 pm. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Hobby Airport to Midway International Airport

The shortest flight time between HOU and MDW is 2 hours and 25 minutes.

ViaTotal flight timeLayover timeDistance
Direct2h 25m-943 miles (1517 km)
OKC Oklahoma City4h 30m1h 50m1115 miles (1794 km)
TUL Tulsa4h 40m1h 5m1041 miles (1675 km)
STL Saint Louis4h 50m2h 35m944 miles (1519 km)
IND Indianapolis5h 0m1h 15m1028 miles (1654 km)
MCI Kansas City5h 0m40m1077 miles (1733 km)
CMH Columbus5h 13m1h 0m1290 miles (2076 km)
MSY New Orleans5h 20m1h 10m1134 miles (1825 km)
AUS Austin5h 20m1h 40m1125 miles (1810 km)
DAL Dallas5h 25m1h 15m1039 miles (1672 km)
BHM Birmingham5h 30m2h 20m1145 miles (1842 km)
MEM Memphis5h 33m2h 35m970 miles (1561 km)
SDF Louisville5h 40m1h 20m1079 miles (1736 km)
PIT Pittsburgh5h 50m2h 50m1540 miles (2478 km)
ATL Atlanta5h 55m2h 0m1292 miles (2079 km)
SAT San Antonio6h 0m2h 55m1234 miles (1986 km)
BNA Nashville6h 0m2h 20m1070 miles (1722 km)
OMA Omaha6h 15m2h 40m1234 miles (1986 km)
SAV Savannah6h 40m2h 10m1618 miles (2603 km)
MSP Minneapolis7h 15m1h 35m1414 miles (2275 km)
MAF Midland7h 50m2h 10m1494 miles (2404 km)
CLT Charlotte8h 30m2h 40m1511 miles (2431 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.HOU-MDW flight routesHouston to Chicago flight routes illustrated on a map.
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Houston - Chicago route map and flight paths
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Show all destinations from HOU Show all destinations from MDW

You can fly non-stop from Houston (HOU) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 2 hours and 25 minutes. If you travel with a connecting flight instead, for example via Oklahoma City, the total flight time will be 4 hours and 30 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Southwest Airlines and Delta Air Lines is also an option.

The flight time between William P. Hobby Airport (HOU) and Chicago Midway International (MDW) is approximately 2 hours and 25 minutes. The distance between the two airports is 1292 miles (or 2079 kilometers).

Yes, you can fly non-stop to MDW from HOU with Southwest Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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