Use the Orange Line train for a quick, affordable trip to MDW, taking less than 30 minutes to reach the city center.

Most accurate provider | CheapOair 3 stars |
|---|---|
Most trusted provider | CheapOair 3 stars |
Round-trip from | $117 (Southwest) |
One-way from | $59 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $224 |
Good round-trip deal | $227 or less |
Good one-way deal | $124 or less |
Fly from
Fly to
Route
Depart
Return
Price
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
qua 2/18
6:15 am-9:15 am
Nonstop3h 00m
Houston Hobby
qua 2/25
8:30 pm-10:55 pm
Nonstop2h 25m
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
dom 1/11
2:15 pm-7:45 pm
1 stop5h 30m
Houston Hobby
dom 1/18
6:15 am-1:30 pm
1 stop7h 15m
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
qua 2/4
8:15 am-2:30 pm
1 stop6h 15m
Houston Hobby
qua 2/11
8:30 pm-10:55 pm
Nonstop2h 25m
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
qua 1/21
9:55 am-4:10 pm
1 stop6h 15m
Houston Hobby
seg 1/26
11:09 am-6:49 pm
1 stop7h 40m
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
qui 1/8
9:55 am-4:10 pm
1 stop6h 15m
Houston Hobby
qui 1/15
5:45 am-10:59 am
1 stop5h 14m
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
ter 1/13
9:55 am-4:10 pm
1 stop6h 15m
Houston Hobby
sáb 1/17
11:09 am-4:44 pm
1 stop5h 35m
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
ter 1/13
9:55 am-4:10 pm
1 stop6h 15m
Houston Hobby
qui 1/15
5:45 am-10:59 am
1 stop5h 14m
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
ter 1/20
11:15 am-4:10 pm
1 stop4h 55m
Houston Hobby
sáb 1/24
11:09 am-4:59 pm
1 stop5h 50m
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
sáb 1/17
11:21 am-4:10 pm
1 stop4h 49m
Houston Hobby
ter 1/20
5:04 pm-10:22 pm
1 stop5h 18m
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
sáb 1/10
11:21 am-4:10 pm
1 stop4h 49m
Houston Hobby
sáb 1/17
11:09 am-4:29 pm
1 stop5h 20m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*2 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars |
Booking 73 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Houston Hobby Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, February is the cheapest month in which you can book a flight from Chicago to Houston Hobby Airport (average of $66). Flying from Chicago to Houston Hobby Airport in July is currently the most expensive (average of $132). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Unlike in the morning, when flights are generally more expensive, you can save up to 26% on flights from Chicago to Houston Hobby Airport by exploring options for tickets in the evening.
Travelers seeking maximum savings on their Chicago to Houston Hobby Airport flight should consider departing on Thursday at noon when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
About 17% of weekly flights between Chicago and Houston have experienced delays in the past year, with the average delay time being 114 minutes.
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Over the last year, Sun Country Air have had the lowest number of delays on this route, with no flights being classified as delayed.
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Overall
Boarding
Comfort
Food
Entertainment
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$71 | Average$174 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$78 | Average$177 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$130 | Average$371 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$165 | Average$272 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$178 | Average$343 | FlexibilityNo cancel fee | On-time63% |