$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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Sep 22 — Sep 291
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 December, booked 79 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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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 August 23, 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 August 23, 2026.
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sat 10/38:25 am -
Nonstop2h 25m
Sat 10/103:10 pm -
Nonstop2h 40m
Deal found 8/19![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 8/19. 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.
Wed 9/164:45 pm -
Nonstop2h 25m
Wed 9/2310:10 am -
1 stop3h 50m
Deal found 8/19![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 8/20. 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.
Thu 10/2910:00 am -
1 stop4h 10m
Mon 11/24:50 pm -
1 stop4h 10m
Deal found 8/20![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 8/19. 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 10/165:00 am -
Nonstop2h 25m
Mon 10/199:30 pm -
Nonstop2h 35m
Deal found 8/19![Southwest logo]()
$222
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 11/612:55 pm -
1 stop4h 05m
Mon 11/99:20 pm -
Nonstop2h 45m
Deal found 8/21![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:26 pm -
1 stop5h 18m
Sat 9/194:30 pm -
1 stop6h 09m
Deal found 8/21![Delta logo]()
$229
This Delta deal was found by Cheapflights users on 8/18. 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.
Sat 10/311:08 am -
1 stop5h 29m
Sat 10/103:15 pm -
1 stop7h 48m
Deal found 8/18![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 8/22. 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.
Sat 10/2412:00 pm -
2 stops5h 45m
Tue 10/271:30 pm -
1 stop5h 25m
Deal found 8/22![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:26 pm -
1 stop5h 18m
Mon 10/56:05 am -
1 stop7h 13m
Deal found 8/21![Delta logo]()
$231
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:26 pm -
1 stop6h 33m
Mon 10/55:30 am -
1 stop7h 48m
Deal found 8/21![Delta logo]()
$231
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 9/117:55 pm -
Nonstop2h 25m
Mon 9/145:30 pm -
Nonstop2h 30m
Deal found 8/21![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 8/18. 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 9/2911:00 am -
1 stop7h 45m
Mon 10/56:10 am -
2 stops10h 15m
Deal found 8/18![Delta logo]()
$234
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 August 23, 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 August 23, 2026.
This Southwest deal was found by Cheapflights users on 8/21. 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.
Tue 9/228:50 pm -
Nonstop2h 25m
Sat 10/247:05 pm -
Nonstop2h 35m
Deal found 8/21![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:09 pm -
1 stop5h 29m
Tue 11/35:05 pm -
1 stop5h 58m
Deal found 8/20![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 10/611:05 am -
1 stop5h 45m
Thu 10/88:15 am -
Nonstop2h 45m
Deal found 8/18![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 8/18. 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 9/85:26 pm -
1 stop6h 33m
Sat 9/123:40 pm -
1 stop6h 59m
Deal found 8/18![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 8/18. 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.
Wed 11/112:35 pm -
Nonstop2h 25m
Fri 11/134:50 pm -
1 stop4h 10m
Deal found 8/18![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:28 pm -
1 stop5h 05m
Tue 11/312:27 pm -
2 stops10h 36m
Deal found 8/20![Delta logo]()
$234
This Southwest deal was found by Cheapflights users on 8/18. 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 11/1212:55 pm -
1 stop4h 05m
Fri 11/134:50 pm -
1 stop4h 10m
Deal found 8/18![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:28 pm -
1 stop6h 29m
Tue 10/131:55 pm -
2 stops9h 08m
Deal found 8/22![Delta logo]()
$234
This Delta deal was found by Cheapflights users on 8/18. 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.
Sat 10/1711:12 am -
2 stops9h 18m
Mon 10/191:25 pm -
2 stops9h 38m
Deal found 8/18![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 9/183:05 pm -
1 stop4h 45m
Tue 9/227:40 am -
2 stops6h 05m
Deal found 8/21![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:08 am -
1 stop5h 57m
Thu 12/1711:28 am -
1 stop5h 02m
Deal found 8/22![Delta logo]()
$242
This Southwest deal was found by Cheapflights users on 8/22. 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.
Thu 11/127:50 am -
Nonstop2h 30m
Sun 11/159:20 pm -
Nonstop2h 45m
Deal found 8/22![Southwest logo]()
$278
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:20 pm -
1 stop6h 39m
Tue 9/228:05 am -
1 stop5h 13m
Deal found 8/21![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 8/20. 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.
Thu 9/245:45 pm -
Nonstop2h 25m
Sun 9/277:30 am -
1 stop6h 00m
Deal found 8/20![Southwest logo]()
$288
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:09 pm -
1 stop5h 29m
Mon 10/191:25 pm -
2 stops9h 38m
Deal found 8/22![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:09 am -
2 stops10h 23m
Fri 10/231:55 pm -
2 stops9h 08m
Deal found 8/20![Delta logo]()
$287
This Delta deal was found by Cheapflights users on 8/18. 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.
Sat 10/1711:12 am -
2 stops9h 18m
Sun 10/186:30 am -
1 stop7h 37m
Deal found 8/18![Delta logo]()
$303
This Delta deal was found by Cheapflights users on 8/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/245:30 pm -
1 stop5h 26m
Fri 12/412:30 pm -
2 stops10h 43m
Deal found 8/19![Delta logo]()
$307
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am -
1 stop6h 40m
Wed 9/910:44 am -
1 stop5h 46m
Deal found 8/22![Delta logo]()
$351
This Delta deal was found by Cheapflights users on 8/18. 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.
Fri 11/136:00 am -
2 stops10h 41m
Mon 11/1611:29 am -
2 stops11h 44m
Deal found 8/18![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 8/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:27 am -
1 stop6h 38m
Sun 11/156:49 am -
1 stop7h 22m
Deal found 8/22![Delta logo]()
$384
This Delta deal was found by Cheapflights users on 8/23. 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.
Tue 9/2911:00 am -
2 stops9h 30m
Wed 9/307:05 am -
2 stops9h 25m
Deal found 8/23![Delta logo]()
$394
Last-minute flights from Galveston to ChicagoDiscover last-minute flight deals from Galveston to Chicago. Data last updated August 23, 2026 and is based on user searches.
Discover last-minute flight deals from Galveston to Chicago. Data last updated August 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 8/19. 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.
Wed 9/98:50 pm -
Nonstop2h 25m
Fri 9/111:05 pm -
1 stop5h 20m
Deal found 8/19![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 9/117:55 pm -
Nonstop2h 25m
Mon 9/145:30 pm -
Nonstop2h 30m
Deal found 8/21![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:26 pm -
1 stop5h 18m
Sat 9/194:30 pm -
1 stop6h 09m
Deal found 8/21![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 9/152:45 pm -
Nonstop2h 25m
Tue 9/222:40 pm -
2 stops5h 20m
Deal found 8/18![Southwest logo]()
$224
This Southwest deal was found by Cheapflights users on 8/18. 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.
Tue 9/1511:25 am -
2 stops5h 30m
Thu 9/175:30 am -
1 stop5h 05m
Deal found 8/18![Southwest logo]()
$234
This Southwest deal was found by Cheapflights users on 8/19. 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.
Wed 9/164:45 pm -
Nonstop2h 25m
Wed 9/2310:10 am -
1 stop3h 50m
Deal found 8/19![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 8/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:26 pm -
1 stop6h 33m
Wed 9/235:30 am -
1 stop7h 48m
Deal found 8/19![Delta logo]()
$229
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 9/185:45 pm -
Nonstop2h 25m
Fri 9/255:25 am -
Nonstop2h 25m
Deal found 8/21![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sat 9/197:00 am -
Nonstop2h 25m
Tue 9/227:50 am -
Nonstop2h 35m
Deal found 8/19![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sat 9/199:45 am -
1 stop6h 20m
Sat 9/267:20 am -
Nonstop2h 30m
Deal found 8/19![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 8/21. 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.
Fri 9/257:55 pm -
Nonstop2h 25m
Mon 9/285:25 am -
Nonstop2h 25m
Deal found 8/21![Southwest logo]()
$222
This Delta deal was found by Cheapflights users on 8/18. 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 9/2911:00 am -
1 stop7h 45m
Mon 10/56:10 am -
2 stops10h 15m
Deal found 8/18![Delta logo]()
$234
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 August 23, 2026.
Search for one-way flight options from Galveston to Chicago. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
This Southwest deal was found by Cheapflights users on 8/18. 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 10/316:00 am -
Nonstop2h 25m
Deal found 8/18![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 8/18. 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 11/1212:55 pm -
1 stop4h 05m
Deal found 8/18![Southwest logo]()
$110
This Delta deal was found by Cheapflights users on 8/18. 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.
Sat 9/195:26 pm -
1 stop5h 18m
Deal found 8/18![Delta logo]()
$115
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2111:12 am -
1 stop7h 59m
Deal found 8/21![Delta logo]()
$115
This Southwest deal was found by Cheapflights users on 8/18. 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.
Fri 9/185:45 pm -
Nonstop2h 25m
Deal found 8/18![Southwest logo]()
$118
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:00 am -
2 stops7h 33m
Deal found 8/21![Delta logo]()
$120
This Delta deal was found by Cheapflights users on 8/18. 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.
Sat 10/316:09 am -
2 stops10h 17m
Deal found 8/18![Delta logo]()
$120
This Southwest deal was found by Cheapflights users on 8/19. 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 11/1312:55 pm -
1 stop4h 05m
Deal found 8/19![Southwest logo]()
$123
This Delta deal was found by Cheapflights users on 8/18. 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 10/206:09 am -
1 stop5h 45m
Deal found 8/18![Delta logo]()
$125
This Delta deal was found by Cheapflights users on 8/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:26 pm -
1 stop6h 33m
Deal found 8/19![Delta logo]()
$125
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:20 pm -
1 stop5h 24m
Deal found 8/21![Delta logo]()
$128
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:20 pm -
1 stop6h 39m
Deal found 8/20![Delta logo]()
$128
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 August 23, 2026.
Round-trip from | $209 (Southwest) |
|---|---|
One-way from | $105 (Southwest) |
Popular in | July |
Cheapest in | January |
Average price | $251 |
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 7,457,451 searches. Data last updated August 23, 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
Quickest round-trip
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Tue 9/22
8:50 pm-11:15 pm
Nonstop2h 25m
Chicago Midway
Sat 10/24
7:05 pm-9:40 pm
Nonstop2h 35m
$209
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Tue 10/6
11:05 am-4:50 pm
1 stop5h 45m
Chicago Midway
Thu 10/8
8:15 am-11:00 am
Nonstop2h 45m
$219
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Wed 11/11
2:35 pm-5:00 pm
Nonstop2h 25m
Chicago Midway
Fri 11/13
4:50 pm-9:00 pm
1 stop4h 10m
$228
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Wed 10/28
3:09 pm-8:38 pm
1 stop5h 29m
Chicago O'Hare Intl
Tue 11/3
5:05 pm-11:03 pm
1 stop5h 58m
$229
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Tue 9/8
5:26 pm-11:59 pm
1 stop6h 33m
Chicago O'Hare Intl
Sat 9/12
3:40 pm-10:39 pm
1 stop6h 59m
$229
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Thu 11/12
12:55 pm-5:00 pm
1 stop4h 05m
Chicago Midway
Fri 11/13
4:50 pm-9:00 pm
1 stop4h 10m
$233
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Wed 10/28
5:28 pm-10:33 pm
1 stop5h 05m
Chicago Midway
Tue 11/3
12:27 pm-11:03 pm
2 stops10h 36m
$234
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Tue 10/6
5:28 pm-11:57 pm
1 stop6h 29m
Chicago O'Hare Intl
Tue 10/13
1:55 pm-11:03 pm
2 stops9h 08m
$234
HoustonChicago
HOU Houston Hobby - ORD Chicago O'Hare Intl
HOUORD
Houston Hobby
Sat 10/17
11:12 am-8:30 pm
2 stops9h 18m
Chicago O'Hare Intl
Mon 10/19
1:25 pm-11:03 pm
2 stops9h 38m
$239
HoustonChicago
HOU Houston Hobby - MDW Chicago Midway
HOUMDW
Houston Hobby
Fri 12/11
6:08 am-12:05 pm
1 stop5h 57m
Chicago Midway
Thu 12/17
11:28 am-4:30 pm
1 stop5h 02m
$242
Showing 1-10 of 48 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 August 23, 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 46% on airfare.
How much does it cost to fly round-trip from Galveston to Chicago?
Airfare is typical for this route at the moment.
Galveston to Chicago flights typically cost between $163 and $343 in October.The cheapest round-trip price found within the last 5 days was $209 on Southwest (Oct 3-Oct 10).
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 August 22, 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. Monday 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 August 23, 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.
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Crew
8.6
Food
7.0
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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
Valparaiso
Hammond
Saint Joseph
Porter
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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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 August 23, 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 August 23, 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 7,457,451 searches. Data last updated August 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$178 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$400 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$177 | Average$296 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$197 | Average$387 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$228 | Average$327 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$268 | Average$309 | FlexibilityNo cancel fee | On-time62% |