$105+ 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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Jul 19 — Jul 261
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 85 days in advance, depart on a Saturday or Wednesday and return on a Wednesday
Cheap flight deals from Galveston to Chicago
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Last-minute
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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 June 19, 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 June 19, 2026.
This Southwest deal was found by Cheapflights users on 6/16. 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 7/142:35 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 7/157:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/16. 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 8/268:50 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Tue 9/110:10 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/16![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 6/17. 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 8/112:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Thu 8/135:30 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/17![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 6/16. 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 7/149:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 7/219:00 am
MDW
- HOU
1 stop5h 00m
Southwest
Deal found 6/16![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 6/16. 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 8/48:50 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Thu 8/61:05 pm
MDW
- HOU
1 stop5h 20m
Southwest
Deal found 6/16![Southwest logo]()
$223
This Southwest deal was found by Cheapflights users on 6/15. 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 7/288:15 am
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 8/47:40 am
MDW
- HOU
2 stops6h 05m
Southwest
Deal found 6/15![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 6/16. 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 8/65:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 8/105:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/16![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 6/16. 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 8/511:25 am
HOU
- MDW
1 stop4h 35m
Southwest
Mon 8/105:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/16![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 6/18. 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 8/611:30 am
HOU
- MDW
2 stops5h 25m
Southwest
Wed 8/128:25 pm
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 6/18![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 6/16. 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 7/285:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Tue 8/46:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/16![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 6/17. 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 8/111:13 pm
HOU
- ORD
1 stop5h 36m
Delta
Thu 8/136:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/17![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 6/17. 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 8/410:50 am
HOU
- ORD
2 stops9h 40m
Delta
Tue 8/117:00 am
ORD
- HOU
2 stops9h 25m
Delta
Deal found 6/17![Delta logo]()
$239
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 June 19, 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 June 19, 2026.
This Southwest deal was found by Cheapflights users on 6/18. 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 8/157:40 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Tue 8/1810:10 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/18![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 6/17. 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 8/410:50 am
HOU
- ORD
2 stops9h 40m
Delta
Tue 8/116:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/17![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 6/17. 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 8/1510:25 am
HOU
- MDW
1 stop3h 50m
Southwest
Sat 8/156:05 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/17![Southwest logo]()
$231
This Southwest deal was found by Cheapflights users on 6/13. 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 9/57:15 am
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 9/87:40 am
MDW
- HOU
2 stops6h 05m
Southwest
Deal found 6/13![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 6/18. 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 7/1410:40 am
HOU
- ORD
2 stops9h 51m
Delta
Wed 7/296:35 am
ORD
- HOU
1 stop5h 35m
Delta
Deal found 6/18![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 6/14. 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 7/278:10 am
HOU
- MDW
Nonstop2h 30m
Southwest
Thu 8/65:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/14![Southwest logo]()
$252
This Delta deal was found by Cheapflights users on 6/17. 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 8/206:00 am
HOU
- ORD
2 stops12h 29m
Delta
Sun 8/235:30 am
ORD
- HOU
1 stop6h 46m
Delta
Deal found 6/17![Delta logo]()
$305
This Southwest deal was found by Cheapflights users on 6/15. 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 7/176:50 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 7/299:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/15![Southwest logo]()
$254
This Delta deal was found by Cheapflights users on 6/13. 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.
Fri 8/281:13 pm
HOU
- ORD
1 stop5h 36m
Delta
Sat 8/297:00 am
ORD
- HOU
2 stops9h 25m
Delta
Deal found 6/13![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 6/17. 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 8/213:50 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 8/241:05 pm
MDW
- HOU
1 stop5h 20m
Southwest
Deal found 6/17![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 6/13. 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.
Sat 7/2511:00 am
HOU
- ORD
1 stop7h 46m
Delta
Tue 7/286:35 am
ORD
- HOU
1 stop5h 35m
Delta
Deal found 6/13![Delta logo]()
$319
This Southwest deal was found by Cheapflights users on 6/15. 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 8/1111:25 am
HOU
- MDW
2 stops5h 30m
Southwest
Mon 8/171:05 pm
MDW
- HOU
1 stop5h 20m
Southwest
Deal found 6/15![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 6/16. 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 8/137:55 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Sun 8/167:20 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/16![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 6/14. 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.
Fri 8/710:50 am
HOU
- ORD
2 stops9h 40m
Delta
Mon 8/106:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/14![Delta logo]()
$357
This Southwest deal was found by Cheapflights users on 6/16. 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 7/115:00 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 7/143:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 6/16![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 6/15. 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 6/301:10 pm
HOU
- ORD
1 stop7h 22m
Delta
Thu 7/26:35 am
ORD
- HOU
1 stop5h 37m
Delta
Deal found 6/15![Delta logo]()
$368
This Southwest deal was found by Cheapflights users on 6/15. 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 8/67:55 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Sun 8/97:30 am
MDW
- HOU
1 stop6h 00m
Southwest
Deal found 6/15![Southwest logo]()
$290
This Delta deal was found by Cheapflights users on 6/16. 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.
Sat 9/56:00 am
HOU
- ORD
2 stops11h 41m
Delta
Tue 9/82:00 pm
ORD
- HOU
2 stops8h 40m
Delta
Deal found 6/16![Delta logo]()
$380
This Southwest deal was found by Cheapflights users on 6/16. 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 7/38:35 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 7/83:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 6/16![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 6/14. 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 9/105:26 pm
HOU
- ORD
1 stop6h 33m
Delta
Mon 9/142:00 pm
ORD
- HOU
2 stops8h 35m
Delta
Deal found 6/14![Delta logo]()
$394
This Southwest deal was found by Cheapflights users on 6/18. 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 7/208:35 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Sun 7/266:55 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/18![Southwest logo]()
$323
This Delta deal was found by Cheapflights users on 6/17. 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.
Fri 8/2110:50 am
HOU
- ORD
2 stops9h 40m
Delta
Sun 8/235:30 am
ORD
- HOU
1 stop6h 46m
Delta
Deal found 6/17![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 6/15. 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 9/310:50 am
HOU
- ORD
2 stops9h 40m
Delta
Fri 9/411:22 am
ORD
- HOU
2 stops10h 43m
Delta
Deal found 6/15![Delta logo]()
$410
Last-minute flights from Galveston to ChicagoDiscover last-minute flight deals from Galveston to Chicago. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from Galveston to Chicago. Data last updated June 19, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/15. 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 7/78:15 am
HOU
- MDW
1 stop5h 35m
Southwest
Tue 7/73:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 6/15![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 6/15. 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 7/82:35 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 7/143:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 6/15![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 6/16. 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 7/142:35 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Wed 7/157:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/16![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/16. 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 7/149:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 7/219:00 am
MDW
- HOU
1 stop5h 00m
Southwest
Deal found 6/16![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 6/15. 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 7/159:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Wed 7/2210:15 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/15![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 6/16. 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 7/159:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Sat 7/188:25 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/16![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 6/17. 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 7/1510:40 am
HOU
- ORD
2 stops9h 51m
Delta
Wed 7/229:45 am
ORD
- HOU
1 stop6h 37m
Delta
Deal found 6/17![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 6/14. 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.
Sat 7/2511:00 am
HOU
- ORD
1 stop6h 12m
Delta
Tue 8/46:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/14![Delta logo]()
$264
This Southwest deal was found by Cheapflights users on 6/14. 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 7/289:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Thu 8/65:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/14![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 6/15. 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 7/288:15 am
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 8/47:40 am
MDW
- HOU
2 stops6h 05m
Southwest
Deal found 6/15![Southwest logo]()
$224
This Delta deal was found by Cheapflights users on 6/16. 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 7/285:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Tue 8/46:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/16![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 6/14. 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 7/285:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Thu 8/66:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/14![Delta logo]()
$237
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 June 19, 2026.
Search for one-way flight options from Galveston to Chicago. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
This Southwest deal was found by Cheapflights users on 6/15. 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 7/144:05 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/15![Southwest logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:11 pm
HOU
- MDW
1 stop19h 48m
Allegiant Air
Deal found 6/16![Allegiant Air logo]()
$109
This Southwest deal was found by Cheapflights users on 6/17. 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 8/1211:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 6/17![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 6/17. 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 8/106:10 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/17![Southwest logo]()
$113
This Delta deal was found by Cheapflights users on 6/16. 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 8/116:00 am
HOU
- MDW
1 stop5h 51m
Delta
Deal found 6/16![Delta logo]()
$115
This Delta deal was found by Cheapflights users on 6/16. 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 8/111:13 pm
HOU
- ORD
1 stop7h 42m
Delta
Deal found 6/16![Delta logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:03 pm
HOU
- MDW
1 stop19h 35m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$116
This Southwest deal was found by Cheapflights users on 6/18. 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 8/810:25 am
HOU
- MDW
1 stop3h 50m
Southwest
Deal found 6/18![Southwest logo]()
$118
This Delta deal was found by Cheapflights users on 6/17. 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 7/1510:40 am
HOU
- ORD
2 stops9h 51m
Delta
Deal found 6/17![Delta logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:11 pm
HOU
- MDW
1 stop19h 48m
Allegiant Air
Deal found 6/17![Allegiant Air logo]()
$121
This Delta deal was found by Cheapflights users on 6/16. 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.
Mon 8/106:00 am
HOU
- MDW
1 stop5h 51m
Delta
Deal found 6/16![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 6/17. 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.
Sat 8/810:50 am
HOU
- ORD
1 stop6h 01m
Delta
Deal found 6/17![Delta logo]()
$123
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 June 19, 2026.
Round-trip from | $209 (Southwest) |
|---|---|
One-way from | $105 (Southwest) |
Popular in | May |
Cheapest in | January |
Average price | $278 |
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 June 19, 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 8/15
7:40 pm-10:00 pm
Nonstop2h 20m
Chicago Midway
Tue 8/18
10:10 am-2:00 pm
1 stop3h 50m
$223
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 8/15
10:25 am-2:15 pm
1 stop3h 50m
Chicago Midway
Sat 8/15
6:05 pm-8:40 pm
Nonstop2h 35m
$231
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 9/5
7:15 am-9:45 am
Nonstop2h 30m
Chicago Midway
Tue 9/8
7:40 am-1:45 pm
2 stops6h 05m
$232
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 8/4
10:50 am-8:30 pm
2 stops9h 40m
Chicago O'Hare Intl
Tue 8/11
6:40 am-12:16 pm
1 stop5h 36m
$234
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 7/27
8:10 am-10:40 am
Nonstop2h 30m
Chicago Midway
Thu 8/6
5:55 am-8:25 am
Nonstop2h 30m
$252
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 7/17
6:50 pm-9:15 pm
Nonstop2h 25m
Chicago Midway
Wed 7/29
9:00 pm-11:40 pm
Nonstop2h 40m
$254
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 8/21
3:50 pm-6:15 pm
Nonstop2h 25m
Chicago Midway
Mon 8/24
1:05 pm-6:25 pm
1 stop5h 20m
$268
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 8/11
11:25 am-4:55 pm
2 stops5h 30m
Chicago Midway
Mon 8/17
1:05 pm-6:25 pm
1 stop5h 20m
$273
Quickest round-trip
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Thu 8/13
7:55 pm-10:15 pm
Nonstop2h 20m
Chicago Midway
Sun 8/16
7:20 am-9:50 am
Nonstop2h 30m
$280
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 7/14
10:40 am-8:31 pm
2 stops9h 51m
Chicago O'Hare Intl
Wed 7/29
6:35 am-12:10 pm
1 stop5h 35m
$289
Showing 1-10 of 53 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
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 June 19, 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 49% on airfare.
How much does it cost to fly round-trip from Galveston to Chicago?
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 June 13, 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 afternoons 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 June 19, 2026.
See what other customers who have flown with Southwest,Delta, andUnited 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.
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Crew
8.6
Overall
7.9
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 locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Alternative routes for Galveston to Chicago
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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 June 19, 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 June 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 5 airlines flying from Galveston to Chicago
Discover the top 5 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 June 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$59 | Average$181 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$389 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$167 | Average$354 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$172 | Average$275 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$349 | FlexibilityNo cancel fee | On-timeN/A |