
Round-trip from | $179 (Southwest) |
|---|---|
One-way from | $90 (Southwest) |
Popular in | March |
Cheapest in | January |
Average price | $245 |
Fly from
Fly to
Route
Depart
Return
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 5/16
8:20 pm-10:45 pm
Nonstop2h 25m
Chicago Midway
Tue 5/19
9:40 am-2:00 pm
1 stop4h 20m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 5/30
3:25 pm-5:50 pm
Nonstop2h 25m
Chicago Midway
Mon 6/1
9:40 pm-12:20 am
Nonstop2h 40m
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 5/19
7:15 am-12:50 pm
1 stop5h 35m
Chicago O'Hare Intl
Tue 5/26
1:35 pm-10:45 pm
1 stop9h 10m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 6/1
2:40 pm-8:25 pm
1 stop5h 45m
Chicago Midway
Wed 6/3
8:00 am-1:55 pm
2 stops5h 55m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 4/20
4:00 pm-9:15 pm
1 stop5h 15m
Chicago Midway
Mon 4/27
4:00 pm-9:05 pm
1 stop5h 05m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 5/9
10:50 am-4:50 pm
2 stops6h 00m
Chicago Midway
Mon 5/11
7:50 am-1:45 pm
2 stops5h 55m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 4/22
7:35 am-11:35 am
1 stop4h 00m
Chicago Midway
Wed 4/29
8:00 am-1:55 pm
2 stops5h 55m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 5/9
10:50 am-4:50 pm
2 stops6h 00m
Chicago Midway
Sat 5/9
6:05 pm-8:50 pm
Nonstop2h 45m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 5/6
6:10 pm-8:35 pm
Nonstop2h 25m
Chicago Midway
Wed 5/13
8:00 am-1:55 pm
2 stops5h 55m
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 4/22
2:40 pm-8:20 pm
2 stops5h 40m
Chicago Midway
Fri 4/24
12:10 pm-2:50 pm
Nonstop2h 40m
To ensure you get the cheapest price possible for a flight from Galveston to Chicago, you should look to book at least 79 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 $60). Flying from Galveston to Chicago in May is currently the most expensive (average of $103). 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 51% on airfare.
Travelers seeking maximum savings on their Galveston to Chicago flight should consider departing on Wednesday afternoons 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.
Crew
Entertainment
Boarding
Comfort
Food
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Entertainment
Boarding
Comfort
Food
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Entertainment
Boarding
Comfort
Food
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Entertainment
Boarding
Comfort
Food
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Entertainment
Boarding
Comfort
Food
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Crew
Entertainment
Boarding
Comfort
Food
Overall
Reviews
Scott,Feb 2026
HOU - FLL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$63 | Average$178 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$72 | Average$161 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$148 | Average$331 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$162 | Average$272 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$165 | Average$261 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$358 | FlexibilityNo cancel fee | On-timeN/A |