$90+ Cheap flights from Galveston, TX to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — CHI
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Find cheap flights from Galveston to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Galveston to Chicago are usually found in January or October, booked 79 days in advance, depart on a 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 June 9, 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 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 8/268:50 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Tue 9/18:25 pm
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 6/8![Southwest logo]()
$180
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 8/410:50 am
HOU
- MDW
1 stop5h 25m
Delta
Tue 8/1110:54 am
MDW
- HOU
1 stop5h 31m
Delta
Deal found 6/8![Delta 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 8/41:13 pm
HOU
- ORD
1 stop7h 42m
Delta
Tue 8/113:25 pm
ORD
- HOU
1 stop6h 40m
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 8/2611:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Mon 8/315:30 pm
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/8![Southwest logo]()
$204
This Delta deal was found by Cheapflights users on 6/9. 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 8/261:13 pm
HOU
- ORD
1 stop7h 42m
Delta
Tue 9/111:22 am
ORD
- HOU
2 stops10h 43m
Delta
Deal found 6/9![Delta logo]()
$204
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.
Thu 9/1711:05 am
HOU
- MDW
1 stop4h 20m
Southwest
Tue 9/228:25 pm
MDW
- HOU
Nonstop2h 25m
Southwest
Deal found 6/7![Southwest logo]()
$208
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 7/146:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 7/219:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/4![Southwest logo]()
$209
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 9/245:45 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 9/292:40 pm
MDW
- HOU
2 stops5h 15m
Southwest
Deal found 6/8![Southwest logo]()
$214
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 7/89:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Wed 7/1510:15 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/4![Southwest logo]()
$215
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 10/288:40 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Sat 10/317:25 am
MDW
- HOU
1 stop6h 20m
Southwest
Deal found 6/8![Southwest logo]()
$216
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 8/203:50 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 8/315:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/8![Southwest logo]()
$217
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 8/2610:50 am
HOU
- ORD
1 stop7h 59m
Delta
Mon 8/316:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/8![Delta logo]()
$218
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 9, 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 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.
Sat 8/297:15 am
HOU
- MDW
Nonstop2h 30m
Southwest
Mon 8/315:55 am
MDW
- HOU
Nonstop2h 30m
Southwest
Deal found 6/8![Southwest logo]()
$217
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.
Tue 9/2911:00 am
HOU
- ORD
1 stop5h 48m
Delta
Wed 9/3012:40 pm
ORD
- HOU
2 stops9h 55m
Delta
Deal found 6/5![Delta logo]()
$244
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:25 pm
HOU
- ORD
1 stop14h 31m
Sun Country Air
Sun 11/297:35 pm
ORD
- HOU
1 stop22h 55m
Sun Country Air
Deal found 6/8![Sun Country Air logo]()
$405
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 7/1510:25 am
HOU
- MDW
1 stop5h 30m
Southwest
Tue 7/2110:15 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/4![Southwest logo]()
$224
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 7/225:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Wed 7/2911:20 am
ORD
- HOU
1 stop5h 02m
Delta
Deal found 6/4![Delta logo]()
$274
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 7/32:55 pm
HOU
- MDW
1 stop4h 40m
Southwest
Tue 7/73:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 6/4![Southwest logo]()
$266
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.
Sat 7/41:00 pm
HOU
- MDW
2 stops5h 55m
Southwest
Wed 7/89:00 am
MDW
- HOU
1 stop5h 00m
Southwest
Deal found 6/8![Southwest logo]()
$270
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.
Fri 8/710:50 am
HOU
- ORD
1 stop7h 59m
Delta
Mon 8/106:40 am
ORD
- HOU
1 stop5h 36m
Delta
Deal found 6/7![Delta logo]()
$309
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 7/79:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Sun 7/126:55 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/8![Southwest logo]()
$280
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 7/2511:00 am
HOU
- ORD
1 stop7h 46m
Delta
Tue 7/285:30 am
ORD
- HOU
1 stop6h 40m
Delta
Deal found 6/8![Delta logo]()
$311
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 6/248:15 am
HOU
- MDW
1 stop5h 35m
Southwest
Tue 6/305:05 am
MDW
- HOU
1 stop5h 40m
Southwest
Deal found 6/8![Southwest logo]()
$298
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.
Mon 7/65:30 pm
HOU
- MDW
1 stop4h 35m
Southwest
Fri 7/105:00 am
MDW
- HOU
1 stop4h 45m
Southwest
Deal found 6/5![Southwest logo]()
$309
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 7/15:08 pm
HOU
- ORD
1 stop6h 51m
Delta
Sat 7/46:30 am
ORD
- HOU
2 stops9h 54m
Delta
Deal found 6/4![Delta logo]()
$374
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.
Thu 7/98:35 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Sun 7/129:40 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/7![Southwest logo]()
$315
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.
Thu 7/26:25 am
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 7/75:05 am
MDW
- HOU
1 stop4h 40m
Southwest
Deal found 6/5![Southwest logo]()
$317
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.
Wed 8/56:00 am
HOU
- ORD
2 stops10h 17m
Delta
Sun 8/95:30 am
ORD
- HOU
1 stop6h 46m
Delta
Deal found 6/7![Delta logo]()
$424
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:50 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Mon 7/139:40 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/6![Southwest logo]()
$325
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 8/1410:50 am
HOU
- ORD
2 stops9h 40m
Delta
Mon 8/175:30 am
ORD
- HOU
1 stop6h 46m
Delta
Deal found 6/8![Delta logo]()
$434
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 7/1011:15 am
HOU
- MDW
1 stop4h 35m
Southwest
Sun 7/126:55 am
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/5![Southwest logo]()
$327
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.
Sat 7/410:16 am
HOU
- ORD
1 stop7h 01m
Delta
Sat 7/118:27 am
ORD
- HOU
2 stops7h 55m
Delta
Deal found 6/6![Delta logo]()
$515
Last-minute flights from Galveston to ChicagoDiscover last-minute flight deals from Galveston to Chicago. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Galveston to Chicago. Data last updated June 9, 2026 and is based on user searches.
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 7/38:35 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 7/710:15 am
MDW
- HOU
1 stop4h 30m
Southwest
Deal found 6/4![Southwest logo]()
$251
This Southwest deal was found by Cheapflights users on 6/9. 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 7/79:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Tue 7/143:10 pm
MDW
- HOU
2 stops5h 30m
Southwest
Deal found 6/9![Southwest logo]()
$220
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 7/79:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Thu 7/99:40 pm
MDW
- HOU
Nonstop2h 35m
Southwest
Deal found 6/4![Southwest logo]()
$244
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 7/89:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Wed 7/1510:15 am
MDW
- HOU
1 stop3h 50m
Southwest
Deal found 6/4![Southwest logo]()
$215
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 7/146:20 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 7/219:00 pm
MDW
- HOU
Nonstop2h 40m
Southwest
Deal found 6/4![Southwest logo]()
$209
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 7/1410:40 am
HOU
- ORD
2 stops9h 51m
Delta
Tue 7/215:30 am
ORD
- HOU
1 stop6h 40m
Delta
Deal found 6/4![Delta logo]()
$244
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 7/155:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Tue 7/216:35 am
ORD
- HOU
1 stop5h 35m
Delta
Deal found 6/4![Delta logo]()
$229
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.
Sat 7/258:45 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Wed 7/2910:15 am
MDW
- HOU
1 stop4h 30m
Southwest
Deal found 6/8![Southwest logo]()
$250
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.
Tue 7/285:17 pm
HOU
- MDW
1 stop4h 58m
Delta
Tue 8/45:10 pm
MDW
- HOU
1 stop4h 55m
Delta
Deal found 6/5![Delta logo]()
$239
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 7/284:05 pm
HOU
- MDW
Nonstop2h 25m
Southwest
Tue 8/47:40 am
MDW
- HOU
2 stops6h 05m
Southwest
Deal found 6/7![Southwest logo]()
$245
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 7/285:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Thu 7/305:30 am
ORD
- HOU
1 stop6h 40m
Delta
Deal found 6/8![Delta logo]()
$264
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 7/295:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Tue 8/45:28 am
ORD
- HOU
1 stop6h 48m
Delta
Deal found 6/4![Delta logo]()
$239
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 9, 2026.
Search for one-way flight options from Galveston to Chicago. 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 8/48:50 pm
HOU
- MDW
Nonstop2h 20m
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 8/410:50 am
HOU
- MDW
1 stop5h 25m
Delta
Deal found 6/8![Delta logo]()
$100
This Delta deal was found by Cheapflights users on 6/9. 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
Deal found 6/9![Delta 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 7/159:25 pm
HOU
- MDW
Nonstop2h 30m
Southwest
Deal found 6/4![Southwest logo]()
$105
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.
Mon 8/107:40 pm
HOU
- MDW
Nonstop2h 20m
Southwest
Deal found 6/7![Southwest logo]()
$109
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 8/1911:25 am
HOU
- MDW
1 stop4h 05m
Southwest
Deal found 6/4![Southwest logo]()
$110
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 6/305:00 pm
HOU
- MDW
1 stop5h 00m
Southwest
Deal found 6/4![Southwest logo]()
$115
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 7/295:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Deal found 6/4![Delta logo]()
$115
This Kiwi.com 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 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 6/6![Allegiant Air logo]()
$116
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 9/12:35 pm
HOU
- MDW
2 stops5h 35m
Southwest
Deal found 6/4![Southwest logo]()
$120
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 7/155:17 pm
HOU
- ORD
1 stop6h 36m
Delta
Deal found 6/4![Delta logo]()
$120
This Southwest 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 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
Deal found 6/6![Southwest 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 9, 2026.
Round-trip from | $180 (Southwest) |
|---|---|
One-way from | $90 (Southwest) |
Popular in | May |
Cheapest in | January |
Average price | $279 |
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 9, 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 - MDW
HOUMDW
Houston Hobby
Sat 8/29
7:15 am-9:45 am
Nonstop2h 30m
Chicago Midway
Mon 8/31
5:55 am-8:25 am
Nonstop2h 30m
$217
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 7/15
10:25 am-3:55 pm
1 stop5h 30m
Chicago Midway
Tue 7/21
10:15 am-2:05 pm
1 stop3h 50m
$224
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Tue 9/29
11:00 am-4:48 pm
1 stop5h 48m
Chicago O'Hare Intl
Wed 9/30
12:40 pm-10:35 pm
2 stops9h 55m
$244
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Fri 7/3
2:55 pm-7:35 pm
1 stop4h 40m
Chicago Midway
Tue 7/7
3:10 pm-8:40 pm
2 stops5h 30m
$266
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Sat 7/4
1:00 pm-6:55 pm
2 stops5h 55m
Chicago Midway
Wed 7/8
9:00 am-2:00 pm
1 stop5h 00m
$270
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Wed 7/22
5:17 pm-11:53 pm
1 stop6h 36m
Chicago O'Hare Intl
Wed 7/29
11:20 am-4:22 pm
1 stop5h 02m
$274
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Tue 7/7
9:25 pm-11:55 pm
Nonstop2h 30m
Chicago Midway
Sun 7/12
6:55 am-9:30 am
Nonstop2h 35m
$280
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Wed 6/24
8:15 am-1:50 pm
1 stop5h 35m
Chicago Midway
Tue 6/30
5:05 am-10:45 am
1 stop5h 40m
$298
HoustonChicago
HOU - ORD
HOUORD
Houston Hobby
Fri 8/7
10:50 am-6:49 pm
1 stop7h 59m
Chicago O'Hare Intl
Mon 8/10
6:40 am-12:16 pm
1 stop5h 36m
$309
HoustonChicago
HOU - MDW
HOUMDW
Houston Hobby
Mon 7/6
5:30 pm-10:05 pm
1 stop4h 35m
Chicago Midway
Fri 7/10
5:00 am-9:45 am
1 stop4h 45m
$309
Showing 1-10 of 49 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 9, 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 50% 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 8, 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 9, 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.
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
7.9
Crew
8.6
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 9, 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 9, 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$179 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$379 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$167 | Average$346 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$172 | Average$276 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$216 | Average$349 | FlexibilityNo cancel fee | On-timeN/A |