
Round-trip from | $117 (Southwest)  | 
|---|---|
One-way from | $59 (Southwest)  | 
Popular in | June | 
Cheapest in | February | 
Average price | $197 | 
Fly from
Fly to
Route
Depart
Return
Price
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 12/3
2:35 pm-5:00 pm
Nonstop2h 25m
Chicago Midway
Wed 12/10
10:15 am-1:10 pm
Nonstop2h 55m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 12/10
6:35 am-9:00 am
Nonstop2h 25m
Chicago Midway
Sun 12/14
5:10 am-7:55 am
Nonstop2h 45m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 12/4
6:00 am-11:20 am
1 stop5h 20m
Chicago Midway
Sat 12/6
5:00 am-7:50 am
Nonstop2h 50m
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Mon 11/24
6:00 am-12:04 pm
1 stop6h 04m
Chicago O'Hare Intl
Thu 11/27
5:23 am-1:28 pm
1 stop8h 05m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 12/12
9:50 pm-12:10 am
Nonstop2h 20m
Chicago Midway
Sun 12/14
9:55 pm-12:35 am
Nonstop2h 40m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 12/11
6:35 am-9:00 am
Nonstop2h 25m
Chicago Midway
Sun 12/14
5:10 am-7:55 am
Nonstop2h 45m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 12/13
6:40 pm-11:47 pm
1 stop5h 07m
Chicago Midway
Mon 12/15
5:29 pm-10:48 pm
1 stop5h 19m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 12/4
6:47 pm-11:47 pm
1 stop5h 00m
Chicago Midway
Sat 12/6
6:00 am-1:28 pm
1 stop7h 28m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 1/22
9:25 am-2:55 pm
1 stop5h 30m
Chicago Midway
Sun 1/25
5:55 am-8:50 am
Nonstop2h 55m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 12/12
6:47 pm-11:47 pm
1 stop5h 00m
Chicago Midway
Sun 12/14
6:00 am-1:28 pm
1 stop7h 28m
To ensure you get the cheapest price possible for a flight from Galveston to Chicago, you should look to book at least 63 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, January is the cheapest month in which you can book a flight from Galveston to Chicago (average of $53). Flying from Galveston to Chicago in May is currently the most expensive (average of $95). 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.
One of the essential ways to save on airfare from Galveston to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 49% on airfare.
Travelers seeking maximum savings on their Galveston to Chicago flight should consider departing on Monday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Overall
Boarding
Entertainment
Crew
Food
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Overall
Boarding
Entertainment
Crew
Food
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Overall
Boarding
Entertainment
Crew
Food
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Overall
Boarding
Entertainment
Crew
Food
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Overall
Boarding
Entertainment
Crew
Food
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
Overall
Boarding
Entertainment
Crew
Food
Comfort
Reviews
Ila,Mar 2025
HOU - DAL
| Airline | Cheapest | Average | Flexibility | On-time | 
|---|---|---|---|---|
| Cheapest$77 | Average$170 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$77 | Average$186 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$160 | Average$265 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$171 | Average$281 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$177 | Average$348 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$216 | Average$346 | FlexibilityNo cancel fee | On-timeN/A |