$90+ Cheap flights from Chicago (CHI) to Galveston, TX
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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HOU
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Galveston 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 Chicago to Galveston are usually found in September or January, booked 88 days in advance, depart on a Wednesday or Monday and return on a Saturday
Cheap flight deals from Chicago to Galveston
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Best
Last-minute
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Cheapest flights from Chicago to GalvestonExplore the most affordable flight options available from Chicago to Galveston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
Explore the most affordable flight options available from Chicago to Galveston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 9, 2026.
This Southwest deal was found by Cheapflights users on 6/8. 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 10/712:55 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Wed 10/148:40 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 6/8. 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 11/47:40 am
MDW
- HOU
1 stop6h 05m
Southwest
Tue 11/108:40 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/8![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 6/8. 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 8/105:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Tue 8/118:50 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$198
This Delta deal was found by Cheapflights users on 6/8. 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 8/1210:33 am
ORD
- HOU
1 stop5h 52m
Delta
Tue 8/1810:50 am
HOU
- ORD
1 stop6h 01m
Delta
Deal found 6/8![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 6/8. 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 8/1210:30 am
MDW
- HOU
Nonstop2h 30m
Southwest
Mon 8/177:40 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 6/8![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 6/8. 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 10/612:15 pm
ORD
- HOU
2 stops9h 28m
Delta
Wed 10/1410:05 am
HOU
- ORD
1 stop6h 32m
Delta
Deal found 6/8![Delta logo]()
$204
This Southwest deal was found by Cheapflights users on 6/4. 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 7/219:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Tue 7/286:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/4![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 6/8. 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 8/106:40 am
ORD
- HOU
1 stop5h 36m
Delta
Tue 8/1110:50 am
HOU
- ORD
1 stop7h 59m
Delta
Deal found 6/8![Delta logo]()
$218
This Delta deal was found by Cheapflights users on 6/8. 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 8/223:25 pm
ORD
- HOU
1 stop5h 58m
Delta
Mon 8/241:13 pm
HOU
- ORD
1 stop7h 42m
Delta
Deal found 6/8![Delta logo]()
$237
This Delta deal was found by Cheapflights users on 6/4. 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 7/143:22 pm
ORD
- HOU
1 stop6h 29m
Delta
Wed 7/155:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Deal found 6/4![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 6/8. 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 9/117:10 am
ORD
- HOU
1 stop4h 54m
Delta
Tue 9/1511:00 am
HOU
- ORD
1 stop5h 48m
Delta
Deal found 6/8![Delta logo]()
$245
This Delta deal was found by Cheapflights users on 6/5. 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 9/216:40 am
ORD
- HOU
1 stop6h 44m
Delta
Wed 9/235:26 pm
HOU
- ORD
1 stop6h 33m
Delta
Deal found 6/5![Delta logo]()
$247
Best flights from Chicago to GalvestonDiscover carefully curated flight deals from Chicago to Galveston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
Discover carefully curated flight deals from Chicago to Galveston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
This Southwest deal was found by Cheapflights users on 6/8. 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 9/32:50 pm
MDW
- HOU
1 stop5h 15m
Southwest
Mon 9/77:20 am
HOU
- MDW
1 stop4h 55m
Southwest
Deal found 6/8![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 6/4. 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 8/2211:22 am
ORD
- HOU
2 stops10h 01m
Delta
Sat 8/2910:50 am
HOU
- ORD
1 stop8h 09m
Delta
Deal found 6/4![Delta logo]()
$270
This Southwest deal was found by Cheapflights users on 6/8. 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 9/45:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Sun 9/66:30 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/8![Southwest logo]()
$277
This Delta deal was found by Cheapflights users on 6/4. 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 8/2210:56 am
MDW
- HOU
1 stop5h 29m
Delta
Sat 8/2910:50 am
HOU
- MDW
1 stop4h 48m
Delta
Deal found 6/4![Delta logo]()
$292
This Southwest deal was found by Cheapflights users on 6/7. 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 9/126:05 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Tue 9/154:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/7![Southwest logo]()
$279
This Delta deal was found by Cheapflights users on 6/5. 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 9/188:05 am
ORD
- HOU
1 stop5h 19m
Delta
Mon 9/216:00 am
HOU
- ORD
2 stops10h 52m
Delta
Deal found 6/5![Delta logo]()
$307
This Southwest deal was found by Cheapflights users on 6/7. 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 7/19:00 am
MDW
- HOU
1 stop5h 00m
Southwest
Sat 7/41:05 pm
HOU
- MDW
1 stop4h 10m
Southwest
Deal found 6/7![Southwest logo]()
$296
This Southwest deal was found by Cheapflights users on 6/5. 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 7/245:00 am
MDW
- HOU
1 stop4h 45m
Southwest
Mon 7/278:30 pm
HOU
- MDW
1 stop4h 35m
Southwest
Deal found 6/5![Southwest logo]()
$309
This Delta deal was found by Cheapflights users on 6/7. 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 8/2711:22 am
ORD
- HOU
2 stops10h 43m
Delta
Sun 8/306:00 am
HOU
- ORD
1 stop6h 40m
Delta
Deal found 6/7![Delta logo]()
$342
This Southwest deal was found by Cheapflights users on 6/4. 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 7/3010:05 am
MDW
- HOU
1 stop3h 45m
Southwest
Sun 8/27:25 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/4![Southwest logo]()
$313
This Delta deal was found by Cheapflights users on 6/8. 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 10/3010:35 am
MDW
- HOU
1 stop5h 55m
Delta
Thu 11/56:00 am
HOU
- MDW
1 stop5h 56m
Delta
Deal found 6/8![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 6/7. 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 8/141:05 pm
MDW
- HOU
1 stop5h 20m
Southwest
Sun 8/165:40 am
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/7![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 6/4. 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 7/102:45 pm
MDW
- HOU
1 stop5h 00m
Southwest
Sun 7/122:25 pm
HOU
- MDW
1 stop5h 25m
Southwest
Deal found 6/4![Southwest logo]()
$337
This Delta deal was found by Cheapflights users on 6/8. 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 8/1411:22 am
ORD
- HOU
2 stops10h 43m
Delta
Sun 8/166:00 am
HOU
- ORD
1 stop6h 40m
Delta
Deal found 6/8![Delta logo]()
$463
This Delta deal was found by Cheapflights users on 6/8. 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 8/137:00 am
ORD
- HOU
2 stops9h 25m
Delta
Sun 8/166:00 am
HOU
- ORD
1 stop8h 09m
Delta
Deal found 6/8![Delta logo]()
$463
This Delta deal was found by Cheapflights users on 6/6. 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 7/3111:30 am
ORD
- HOU
2 stops10h 21m
Delta
Sun 8/96:00 am
HOU
- ORD
1 stop8h 09m
Delta
Deal found 6/6![Delta logo]()
$473
This Delta deal was found by Cheapflights users on 6/7. 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 10/47:01 am
ORD
- HOU
2 stops9h 30m
Delta
Sat 10/106:00 am
HOU
- ORD
2 stops10h 49m
Delta
Deal found 6/7![Delta logo]()
$579
This Delta deal was found by Cheapflights users on 6/4. 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 7/171:44 pm
ORD
- HOU
1 stop8h 07m
Delta
Sat 7/186:00 am
HOU
- ORD
2 stops9h 05m
Delta
Deal found 6/4![Delta logo]()
$645
This Delta deal was found by Cheapflights users on 6/8. 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 10/3012:15 pm
ORD
- HOU
2 stops9h 28m
Delta
Thu 11/56:00 am
HOU
- ORD
2 stops10h 33m
Delta
Deal found 6/8![Delta logo]()
$649
This Delta deal was found by Cheapflights users on 6/8. 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 6/207:01 am
ORD
- HOU
2 stops9h 26m
Delta
Sun 6/286:03 am
HOU
- ORD
1 stop6h 33m
Delta
Deal found 6/8![Delta logo]()
$651
Last-minute flights from Chicago to GalvestonDiscover last-minute flight deals from Chicago to Galveston. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Galveston. Data last updated June 9, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/5. 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 6/301:10 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Fri 7/36:50 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/5![Southwest logo]()
$245
This Southwest deal was found by Cheapflights users on 6/4. 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 7/112:00 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Sat 7/46:15 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/4![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 6/8. 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 7/15:30 am
ORD
- HOU
1 stop6h 42m
Delta
Sat 7/410:16 am
HOU
- ORD
1 stop7h 01m
Delta
Deal found 6/8![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 6/5. 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 7/41:49 pm
ORD
- HOU
1 stop7h 54m
Delta
Tue 7/710:40 am
HOU
- ORD
1 stop8h 05m
Delta
Deal found 6/5![Delta logo]()
$274
This Delta deal was found by Cheapflights users on 6/5. 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 7/109:45 am
ORD
- HOU
1 stop6h 37m
Delta
Tue 7/145:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Deal found 6/5![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 6/4. 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 7/143:22 pm
ORD
- HOU
1 stop6h 29m
Delta
Wed 7/155:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Deal found 6/4![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 6/4. 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 7/219:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Tue 7/286:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Deal found 6/4![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 6/4. 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 7/2810:15 am
MDW
- HOU
1 stop4h 30m
Southwest
Tue 8/411:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 6/4![Southwest logo]()
$220
This American Airlines deal was found by Cheapflights users on 6/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:04 am
ORD
- HOU
1 stop6h 12m
American Airlines
Tue 8/46:49 pm
HOU
- ORD
1 stop5h 54m
American Airlines
Deal found 6/4![American Airlines logo]()
$282
This Southwest deal was found by Cheapflights users on 6/8. 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 7/2910:15 am
MDW
- HOU
Nonstop2h 40m
Southwest
Wed 8/52:00 pm
HOU
- MDW
1 stop5h 15m
Southwest
Deal found 6/8![Southwest logo]()
$239
This Delta deal was found by Cheapflights users on 6/8. 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 7/296:35 am
ORD
- HOU
1 stop5h 35m
Delta
Wed 8/51:13 pm
HOU
- ORD
1 stop7h 42m
Delta
Deal found 6/8![Delta logo]()
$249
This Delta deal was found by Cheapflights users on 6/4. 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 7/2911:20 am
ORD
- HOU
1 stop5h 02m
Delta
Mon 8/36:00 am
HOU
- ORD
1 stop6h 40m
Delta
Deal found 6/4![Delta logo]()
$264
One-way flights from Chicago to GalvestonSearch for one-way flight options from Chicago to Galveston. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
Search for one-way flight options from Chicago to Galveston. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Southwest deal was found by Cheapflights users on 6/7. 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 9/18:25 pm
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 6/7![Southwest logo]()
$90
This Delta deal was found by Cheapflights users on 6/8. 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 8/113:25 pm
ORD
- HOU
1 stop6h 40m
Delta
Deal found 6/8![Delta logo]()
$100
This Southwest deal was found by Cheapflights users on 6/8. 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 8/44:40 pm
MDW
- HOU
1 stop6h 05m
Southwest
Deal found 6/8![Southwest logo]()
$100
This Southwest deal was found by Cheapflights users on 6/4. 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 7/17:10 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/4![Southwest logo]()
$105
This Southwest deal was found by Cheapflights users on 6/8. 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 8/105:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/8![Southwest logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 6/8. 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 8/162:49 pm
MDW
- HOU
1 stop28h 24m
Allegiant Air
Deal found 6/8![Allegiant Air logo]()
$112
This Delta deal was found by Cheapflights users on 6/4. 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 6/305:30 am
ORD
- HOU
1 stop6h 42m
Delta
Deal found 6/4![Delta logo]()
$115
This Southwest deal was found by Cheapflights users on 6/4. 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 6/303:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 6/4![Southwest logo]()
$115
This Delta deal was found by Cheapflights users on 6/8. 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 9/107:10 am
ORD
- HOU
1 stop4h 54m
Delta
Deal found 6/8![Delta logo]()
$119
This Delta deal was found by Cheapflights users on 6/8. 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 9/106:00 am
MDW
- HOU
1 stop6h 04m
Delta
Deal found 6/8![Delta logo]()
$119
This Delta deal was found by Cheapflights users on 6/4. 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 8/45:28 am
ORD
- HOU
1 stop6h 48m
Delta
Deal found 6/4![Delta logo]()
$120
This Southwest deal was found by Cheapflights users on 6/4. 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 8/245:30 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/4![Southwest logo]()
$123
Find flight deals from Chicago to Galveston
Keep the following information in mind while searching for Chicago to Galveston flight deals. Data was last updated June 9, 2026.
Round-trip from | $180 (Southwest) |
|---|---|
One-way from | $90 (Southwest) |
Popular in | March |
Cheapest in | September |
Average price | $293 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Galveston 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 9, 2026.
Use the filters below to find and compare flights from Chicago to Galveston that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Thu 9/3
2:50 pm-8:05 pm
1 stop5h 15m
Houston Hobby
Mon 9/7
7:20 am-12:15 pm
1 stop4h 55m
$268
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
Sat 8/22
11:22 am-9:23 pm
2 stops10h 01m
Houston Hobby
Sat 8/29
10:50 am-6:59 pm
1 stop8h 09m
$270
Quickest round-trip
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Fri 9/4
5:55 am-8:25 am
Nonstop2h 30m
Houston Hobby
Sun 9/6
6:30 am-8:55 am
Nonstop2h 25m
$277
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Sat 9/12
6:05 pm-8:40 pm
Nonstop2h 35m
Houston Hobby
Tue 9/15
4:45 pm-7:10 pm
Nonstop2h 25m
$279
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Sat 8/22
10:56 am-4:25 pm
1 stop5h 29m
Houston Hobby
Sat 8/29
10:50 am-3:38 pm
1 stop4h 48m
$292
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Wed 7/1
9:00 am-2:00 pm
1 stop5h 00m
Houston Hobby
Sat 7/4
1:05 pm-5:15 pm
1 stop4h 10m
$296
ChicagoHouston
ORD - HOU
ORDHOU
Chicago O'Hare Intl
Fri 9/18
8:05 am-1:24 pm
1 stop5h 19m
Houston Hobby
Mon 9/21
6:00 am-4:52 pm
2 stops10h 52m
$307
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Fri 7/24
5:00 am-9:45 am
1 stop4h 45m
Houston Hobby
Mon 7/27
8:30 pm-1:05 am
1 stop4h 35m
$309
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Thu 7/30
10:05 am-1:50 pm
1 stop3h 45m
Houston Hobby
Sun 8/2
7:25 am-9:50 am
Nonstop2h 25m
$313
ChicagoHouston
MDW - HOU
MDWHOU
Chicago Midway
Fri 8/14
1:05 pm-6:25 pm
1 stop5h 20m
Houston Hobby
Sun 8/16
5:40 am-8:05 am
Nonstop2h 25m
$324
Showing 1-10 of 38 resultsSorted by cheapest first
Best time to book a flight from Chicago to Galveston
Have a flexible travel schedule? Discover the best time to fly to Galveston from Chicago with our price prediction graph.
MDW-HOU
ORD-HOU
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 Chicago to Galveston
CHI-G4L
MDW-HOU
ORD-HOU
What is the cheapest time of day to fly from CHI to G4L?
Find hourly flight availability from Chicago to Galveston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 9, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago to Galveston at noon. If you’re flexible enough to do this you can expect to save up to 8% on your trip compared to booking a flight in the evening.
How much does it cost to fly round-trip from Chicago to Galveston?
What is the cheapest day to fly from Chicago to Galveston?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Galveston. Price data was last updated on May 30, 2026.
Travelers seeking maximum savings on their Chicago to Galveston flight should consider departing on Tuesday mornings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Galveston
Get insights into the airlines that provide service to Galveston. 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 Galveston. Reviews last updated June 9, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago to Galveston by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Food
7.0
Boarding
8.1
Entertainment
7.5
Overall
7.9
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Related info for your journey
Find useful and relevant information for your journey from Chicago to Galveston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
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Chicago and Galveston flights
Browse other Chicago and Galveston flight options. Last updated on June 9, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on June 9, 2026.
Popular flight searches
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Chicago to Galveston flights
Consider these flights traveling from Chicago to Galveston.
Top 5 airlines flying from Chicago to Galveston
Discover the top 5 airlines that operate flights from Chicago to Galveston. 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$57 | Average$182 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$342 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$161 | Average$267 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$197 | Average$302 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$207 | Average$287 | FlexibilityNo cancel fee | On-timeN/A |