$90+ Cheap flights from Galveston, TX to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Apr 24 — May 11
Round-trip
1 adult, Economy
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Find cheap flights from Galveston to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Galveston to Chicago are usually found in January or October, booked 79 days in advance, depart on a Wednesday or Saturday and return on a Wednesday
Cheap flight deals from Galveston to Chicago
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Cheapest flights from Galveston to ChicagoExplore the most affordable flight options available from Galveston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2026.
Explore the most affordable flight options available from Galveston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2026.
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 4/158:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/24![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:15 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 4/288:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/22![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 4/218:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/24![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:00 am
HOU
- MDW
1 stop4h 25m
Southwest
Wed 5/2712:15 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/23![Southwest logo]()
$190
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Thu 4/309:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/23![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:23 pm
HOU
- MDW
1 stop5h 05m
Delta
Wed 4/156:00 am
MDW
- HOU
1 stop6h 40m
Delta
Deal found 3/24![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:15 am
HOU
- ORD
1 stop5h 35m
Southwest
Tue 4/2811:55 am
ORD
- HOU
1 stop4h 55m
Southwest
Deal found 3/24![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
HOU
- ORD
2 stops6h 50m
Southwest
Wed 4/152:40 pm
ORD
- HOU
1 stop5h 15m
Southwest
Deal found 3/24![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:30 am
HOU
- ORD
1 stop6h 00m
Southwest
Tue 4/211:35 pm
ORD
- HOU
1 stop9h 10m
Southwest
Deal found 3/24![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:30 pm
HOU
- ORD
1 stop9h 25m
Southwest
Thu 4/167:35 pm
ORD
- HOU
1 stop13h 00m
Southwest
Deal found 3/24![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:00 am
HOU
- ORD
1 stop7h 30m
Southwest
Sat 4/252:05 pm
ORD
- HOU
1 stop7h 00m
Southwest
Deal found 3/24![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 am
HOU
- ORD
1 stop10h 05m
Southwest
Wed 6/36:15 am
ORD
- HOU
2 stops12h 00m
Southwest
Deal found 3/24![Southwest logo]()
$219
Best flights from Galveston to ChicagoDiscover carefully curated flight deals from Galveston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 25, 2026.
Discover carefully curated flight deals from Galveston to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 25, 2026.
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/168:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 5/199:40 am
MDW
- HOU
1 stop4h 20m
Southwest
Deal found 3/23![Southwest logo]()
$195
This Delta deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/910:40 am
HOU
- ORD
1 stop8h 05m
Delta
Sat 7/113:35 pm
ORD
- HOU
1 stop6h 16m
Delta
Deal found 3/23![Delta logo]()
$328
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:25 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 6/19:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/23![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/197:15 am
HOU
- ORD
1 stop5h 35m
Southwest
Tue 5/261:35 pm
ORD
- HOU
1 stop9h 10m
Southwest
Deal found 3/24![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:40 pm
HOU
- MDW
1 stop5h 45m
Southwest
Wed 6/38:00 am
MDW
- HOU
2 stops5h 55m
Southwest
Deal found 3/24![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:00 pm
HOU
- MDW
1 stop5h 15m
Southwest
Mon 4/274:00 pm
MDW
- HOU
1 stop5h 05m
Southwest
Deal found 3/23![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:50 am
HOU
- MDW
2 stops6h 00m
Southwest
Mon 5/117:50 am
MDW
- HOU
2 stops5h 55m
Southwest
Deal found 3/23![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:35 am
HOU
- MDW
1 stop4h 00m
Southwest
Wed 4/298:00 am
MDW
- HOU
2 stops5h 55m
Southwest
Deal found 3/24![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:50 am
HOU
- MDW
2 stops6h 00m
Southwest
Sat 5/96:05 pm
MDW
- HOU
Nonstop2h 45m
Southwest
Deal found 3/21![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:10 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 5/138:00 am
MDW
- HOU
2 stops5h 55m
Southwest
Deal found 3/21![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/222:40 pm
HOU
- MDW
2 stops5h 40m
Southwest
Fri 4/2412:10 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/22![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:00 am
HOU
- ORD
1 stop5h 10m
Southwest
Sun 5/102:40 pm
ORD
- HOU
1 stop7h 45m
Southwest
Deal found 3/24![Southwest logo]()
$238
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/611:10 am
HOU
- ORD
2 stops11h 45m
Southwest
Wed 5/1311:55 am
ORD
- HOU
1 stop5h 55m
Southwest
Deal found 3/21![Southwest logo]()
$242
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
HOU
- ORD
1 stop5h 10m
Southwest
Fri 4/243:45 pm
ORD
- HOU
2 stops7h 25m
Southwest
Deal found 3/22![Southwest logo]()
$244
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/110:25 am
HOU
- MDW
1 stop5h 25m
Southwest
Sat 5/212:55 pm
MDW
- HOU
1 stop4h 20m
Southwest
Deal found 3/20![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:05 am
HOU
- ORD
2 stops10h 45m
Southwest
Sat 5/212:15 pm
ORD
- HOU
1 stop7h 20m
Southwest
Deal found 3/20![Southwest logo]()
$262
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/306:10 am
HOU
- ORD
1 stop8h 20m
Southwest
Mon 6/12:40 pm
ORD
- HOU
2 stops8h 30m
Southwest
Deal found 3/23![Southwest logo]()
$263
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:10 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 6/99:10 am
MDW
- HOU
1 stop4h 40m
Southwest
Deal found 3/21![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:05 am
HOU
- ORD
2 stops10h 45m
Southwest
Sun 5/33:45 pm
ORD
- HOU
2 stops7h 20m
Southwest
Deal found 3/19![Southwest logo]()
$287
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:10 am
HOU
- ORD
2 stops11h 45m
Southwest
Mon 4/133:45 pm
ORD
- HOU
2 stops7h 25m
Southwest
Deal found 3/24![Southwest logo]()
$347
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/76:00 am
HOU
- ORD
2 stops6h 50m
Southwest
Sat 4/112:05 pm
ORD
- HOU
1 stop5h 30m
Southwest
Deal found 3/23![Southwest logo]()
$368
Last-minute flights from Galveston to ChicagoDiscover last-minute flight deals from Galveston to Chicago. Data last updated March 25, 2026 and is based on user searches.
Discover last-minute flight deals from Galveston to Chicago. Data last updated March 25, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:23 pm
HOU
- MDW
1 stop5h 05m
Delta
Wed 4/156:00 am
MDW
- HOU
1 stop6h 40m
Delta
Deal found 3/24![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/142:30 pm
HOU
- ORD
1 stop9h 25m
Southwest
Thu 4/167:35 pm
ORD
- HOU
1 stop13h 00m
Southwest
Deal found 3/24![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 4/158:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/24![Southwest logo]()
$179
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
HOU
- ORD
2 stops6h 50m
Southwest
Wed 4/152:40 pm
ORD
- HOU
1 stop5h 15m
Southwest
Deal found 3/24![Southwest logo]()
$204
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 4/218:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/24![Southwest logo]()
$188
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:30 am
HOU
- ORD
1 stop6h 00m
Southwest
Tue 4/211:35 pm
ORD
- HOU
1 stop9h 10m
Southwest
Deal found 3/24![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:30 am
HOU
- ORD
1 stop6h 00m
Southwest
Mon 4/203:45 pm
ORD
- HOU
2 stops7h 25m
Southwest
Deal found 3/24![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/219:15 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 4/288:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/22![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:15 am
HOU
- ORD
1 stop5h 35m
Southwest
Tue 4/2811:55 am
ORD
- HOU
1 stop4h 55m
Southwest
Deal found 3/24![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Thu 4/309:40 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 3/23![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 4/274:00 pm
MDW
- HOU
1 stop5h 05m
Southwest
Deal found 3/24![Southwest logo]()
$207
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/238:00 am
HOU
- ORD
1 stop7h 30m
Southwest
Mon 4/274:15 pm
ORD
- HOU
1 stop5h 00m
Southwest
Deal found 3/24![Southwest logo]()
$217
One-way flights from Galveston to ChicagoSearch for one-way flight options from Galveston to Chicago. Find affordable one-way fares based on user searches. Data last updated March 25, 2026.
Search for one-way flight options from Galveston to Chicago. Find affordable one-way fares based on user searches. Data last updated March 25, 2026.
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:40 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 3/23![Southwest logo]()
$90
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 3/24![Southwest logo]()
$99
This Delta deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:23 pm
HOU
- MDW
1 stop5h 05m
Delta
Deal found 3/24![Delta logo]()
$100
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:45 am
HOU
- ORD
1 stop10h 05m
Southwest
Deal found 3/24![Southwest logo]()
$100
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:10 am
HOU
- MDW
1 stop4h 00m
Southwest
Deal found 3/23![Southwest logo]()
$104
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
HOU
- ORD
2 stops6h 50m
Southwest
Deal found 3/23![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:00 am
HOU
- ORD
1 stop7h 30m
Southwest
Deal found 3/24![Southwest logo]()
$109
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:50 am
HOU
- MDW
2 stops6h 00m
Southwest
Deal found 3/23![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:10 am
HOU
- MDW
1 stop4h 00m
Southwest
Deal found 3/21![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:00 am
HOU
- ORD
2 stops7h 15m
Southwest
Deal found 3/24![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:35 am
HOU
- ORD
2 stops9h 55m
Southwest
Deal found 3/23![Southwest logo]()
$115
This Southwest deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:10 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 3/23![Southwest logo]()
$117
Find flight deals from Galveston to Chicago
Keep the following information in mind while searching for Galveston to Chicago flight deals. Data was last updated March 25, 2026.
Round-trip from | $179 (Southwest) |
|---|---|
One-way from | $90 (Southwest) |
Popular in | March |
Cheapest in | January |
Average price | $245 |
Cheapflights Fare Finder
Customize your flight search to find flights from Galveston to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 25, 2026.
Use the filters below to find and compare flights from Galveston to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
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
$195
Quickest round-trip
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
$197
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
$199
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
$213
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
$217
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
$223
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
$223
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
$228
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
$232
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
$234
Showing 1-10 of 51 resultsSorted by cheapest first
Best time to book a flight from Galveston to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Galveston with our price prediction graph.
HOU-MDW
HOU-ORD
HOU-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Galveston to Chicago
G4L-CHI
HOU-MDW
HOU-ORD
HOU-RFD
How far ahead should I book a flight from Galveston to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from Galveston to Chicago. Price data was last updated on March 13, 2026.
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.
What is the cheapest month to book a flight from Galveston to Chicago?
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.
What is the cheapest time of day to fly from G4L to CHI?
Find hourly flight availability from Galveston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 25, 2026.
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.
What is the cheapest day to fly from Galveston to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Galveston to Chicago. Price data was last updated on March 14, 2026.
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.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated March 25, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Galveston to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Galveston to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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Alternative routes for Galveston to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on March 25, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Galveston to Chicago by cabin class
Find flights from Galveston to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Galveston and Chicago flights
Browse other Galveston and Chicago flight options. Last updated on March 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Galveston to Chicago
Discover the top 6 airlines that operate flights from Galveston to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 25, 2026.
| 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 |