$63+ Cheap flights from Chicago (CHI) to Gulf Shores, AL
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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Mar 6 — Mar 131
1 adult, Economy
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Find cheap flights from Chicago to Gulf Shores 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 Gulf Shores are usually found in September or November, booked 62 days in advance, depart on a Tuesday or Wednesday and return on a Thursday
Cheap flight deals from Chicago to Gulf Shores
Cheapest
Best
Last-minute
One-way
Cheapest flights from Chicago to Gulf ShoresExplore the most affordable flight options available from Chicago to Gulf Shores. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
Explore the most affordable flight options available from Chicago to Gulf Shores. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/38:15 am
MDW
- PNS
1 stop7h 00m
Southwest
Tue 3/105:20 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 2/3![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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.
Tue 3/1712:45 pm
ORD
- PNS
1 stop8h 29m
Spirit Airlines
Wed 3/182:15 pm
PNS
- ORD
1 stop9h 02m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 3/18:16 pm
ORD
- PNS
2 stops21h 26m
Multiple Airlines
Sun 3/86:37 pm
PNS
- ORD
1 stop20h 51m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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.
Mon 2/169:22 pm
MDW
- PNS
1 stop20h 20m
Multiple Airlines
Thu 2/196:37 pm
PNS
- MDW
1 stop19h 49m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$219
This CheapOair deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/124:16 pm
ORD
- PNS
1 stop25h 59m
Multiple Airlines
Wed 2/185:20 pm
PNS
- ORD
1 stop6h 27m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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.
Sat 2/218:00 am
MDW
- PNS
1 stop9h 42m
Multiple Airlines
Wed 2/256:37 pm
PNS
- MDW
2 stops26h 35m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$220
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:58 pm
ORD
- PNS
3 stops23h 44m
Spirit Airlines
Tue 3/106:37 pm
PNS
- ORD
2 stops16h 45m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/88:00 am
MDW
- PNS
1 stop9h 42m
Multiple Airlines
Fri 3/132:15 pm
PNS
- MDW
2 stops9h 36m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$221
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/910:48 am
ORD
- PNS
1 stop5h 49m
Spirit Airlines
Sat 2/145:20 pm
PNS
- ORD
1 stop6h 27m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$221
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/39:50 am
MDW
- PNS
2 stops8h 35m
Southwest
Fri 3/65:25 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 2/3![Southwest logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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.
Sat 2/2110:44 am
ORD
- PNS
1 stop6h 58m
Multiple Airlines
Wed 2/256:37 pm
PNS
- ORD
2 stops23h 52m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$222
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:55 pm
MDW
- PNS
Nonstop2h 15m
Southwest
Sat 4/118:00 am
PNS
- MDW
2 stops6h 35m
Southwest
Deal found 2/1![Southwest logo]()
$223
Best flights from Chicago to Gulf ShoresDiscover carefully curated flight deals from Chicago to Gulf Shores that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
Discover carefully curated flight deals from Chicago to Gulf Shores that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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 3/36:00 am
MDW
- PNS
1 stop3h 50m
Southwest
Tue 3/105:20 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 2/3![Southwest logo]()
$217
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/116:07 pm
MDW
- PNS
1 stop5h 06m
Delta
Sun 3/156:00 am
PNS
- MDW
1 stop3h 56m
Delta
Deal found 2/2![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:02 pm
ORD
- PNS
Nonstop2h 26m
United Airlines
Thu 3/127:00 am
PNS
- ORD
Nonstop2h 38m
United Airlines
Deal found 2/2![United Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 3/126:07 pm
MDW
- PNS
1 stop3h 57m
Delta
Sun 3/156:00 am
PNS
- MDW
1 stop3h 56m
Delta
Deal found 2/1![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/13:35 pm
MDW
- PNS
1 stop4h 30m
Southwest
Wed 4/87:40 am
PNS
- MDW
1 stop5h 50m
Southwest
Deal found 2/3![Southwest logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:50 am
ORD
- PNS
Nonstop2h 26m
United Airlines
Mon 3/162:18 pm
PNS
- ORD
Nonstop2h 39m
United Airlines
Deal found 2/3![United Airlines logo]()
$247
This Delta deal was found by Cheapflights users on 2/4. 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.
Thu 3/126:07 pm
MDW
- PNS
1 stop3h 57m
Delta
Tue 3/176:00 am
PNS
- MDW
1 stop6h 02m
Delta
Deal found 2/4![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:35 pm
MDW
- PNS
1 stop4h 45m
Southwest
Sat 4/118:00 am
PNS
- MDW
2 stops6h 35m
Southwest
Deal found 2/1![Southwest logo]()
$233
This Delta deal was found by Cheapflights users on 2/4. 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.
Mon 3/96:07 pm
MDW
- PNS
1 stop3h 57m
Delta
Tue 3/176:00 am
PNS
- MDW
1 stop3h 56m
Delta
Deal found 2/4![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:05 pm
ORD
- PNS
Nonstop2h 25m
United Airlines
Sat 3/212:18 pm
PNS
- ORD
Nonstop2h 39m
United Airlines
Deal found 2/2![United Airlines logo]()
$262
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:15 pm
MDW
- PNS
1 stop8h 05m
Southwest
Sat 4/189:40 am
PNS
- MDW
1 stop4h 45m
Southwest
Deal found 2/1![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 2/4. 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 3/116:00 am
MDW
- PNS
1 stop4h 06m
Delta
Tue 3/176:00 am
PNS
- MDW
1 stop3h 56m
Delta
Deal found 2/4![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:05 pm
ORD
- PNS
Nonstop2h 25m
United Airlines
Fri 3/207:00 am
PNS
- ORD
Nonstop2h 38m
United Airlines
Deal found 2/2![United Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 2/4. 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.
Thu 3/126:07 pm
MDW
- PNS
1 stop3h 57m
Delta
Thu 3/196:00 am
PNS
- MDW
1 stop3h 56m
Delta
Deal found 2/4![Delta logo]()
$227
This Southwest deal was found by Cheapflights users on 2/4. 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 4/311:15 am
MDW
- PNS
2 stops9h 30m
Southwest
Thu 4/95:20 pm
PNS
- MDW
1 stop6h 10m
Southwest
Deal found 2/4![Southwest logo]()
$252
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:02 pm
ORD
- PNS
Nonstop2h 26m
United Airlines
Fri 3/137:00 am
PNS
- ORD
Nonstop2h 38m
United Airlines
Deal found 2/2![United Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 2/4. 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 3/115:30 am
ORD
- PNS
1 stop4h 36m
Delta
Tue 3/173:55 pm
PNS
- ORD
1 stop5h 15m
Delta
Deal found 2/4![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/136:05 pm
ORD
- PNS
Nonstop2h 25m
United Airlines
Sat 3/149:10 am
PNS
- ORD
Nonstop2h 38m
United Airlines
Deal found 2/4![United Airlines logo]()
$262
This Delta deal was found by Cheapflights users on 2/4. 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 3/105:30 am
ORD
- PNS
1 stop5h 41m
Delta
Thu 3/196:00 am
PNS
- ORD
1 stop4h 00m
Delta
Deal found 2/4![Delta logo]()
$227
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1210:50 am
ORD
- PNS
Nonstop2h 26m
United Airlines
Sun 3/157:00 am
PNS
- ORD
Nonstop2h 38m
United Airlines
Deal found 2/2![United Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/2710:49 am
MDW
- PNS
1 stop4h 05m
Delta
Sun 3/16:00 am
PNS
- MDW
1 stop3h 54m
Delta
Deal found 2/1![Delta logo]()
$253
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:02 pm
ORD
- PNS
Nonstop2h 26m
United Airlines
Thu 3/197:00 am
PNS
- ORD
Nonstop2h 38m
United Airlines
Deal found 2/2![United Airlines logo]()
$311
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2310:40 am
ORD
- PNS
Nonstop2h 27m
United Airlines
Sat 2/282:10 pm
PNS
- ORD
Nonstop2h 39m
United Airlines
Deal found 2/2![United Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 2/115:30 am
ORD
- PNS
1 stop4h 56m
Delta
Sun 2/156:00 am
PNS
- ORD
1 stop4h 08m
Delta
Deal found 2/1![Delta logo]()
$302
Last-minute flights from Chicago to Gulf ShoresDiscover last-minute flight deals from Chicago to Gulf Shores. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Gulf Shores. Data last updated February 4, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/910:48 am
ORD
- PNS
1 stop5h 49m
Spirit Airlines
Sat 2/145:20 pm
PNS
- ORD
1 stop6h 27m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$221
This CheapOair deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/124:16 pm
ORD
- PNS
1 stop25h 59m
Multiple Airlines
Wed 2/185:20 pm
PNS
- ORD
1 stop6h 27m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/147:00 am
ORD
- PNS
1 stop8h 54m
Spirit Airlines
Wed 2/185:20 pm
PNS
- ORD
1 stop6h 27m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” 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.
Mon 2/169:22 pm
MDW
- PNS
1 stop20h 20m
Multiple Airlines
Thu 2/196:37 pm
PNS
- MDW
1 stop19h 49m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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.
Sat 2/218:00 am
MDW
- PNS
1 stop9h 42m
Multiple Airlines
Wed 2/256:37 pm
PNS
- MDW
2 stops26h 35m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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.
Sat 2/2110:44 am
ORD
- PNS
1 stop6h 58m
Multiple Airlines
Wed 2/256:37 pm
PNS
- ORD
2 stops23h 52m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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 3/18:16 pm
ORD
- PNS
2 stops21h 26m
Multiple Airlines
Sun 3/86:37 pm
PNS
- ORD
1 stop20h 51m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$218
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:16 pm
ORD
- PNS
2 stops21h 26m
Spirit Airlines
Mon 3/96:37 pm
PNS
- ORD
3 stops26h 36m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$224
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/32:35 pm
MDW
- PNS
1 stop3h 50m
Southwest
Fri 3/65:25 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 2/2![Southwest logo]()
$217
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:58 pm
ORD
- PNS
3 stops23h 44m
Spirit Airlines
Tue 3/106:37 pm
PNS
- ORD
2 stops16h 45m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 3/88:00 am
MDW
- PNS
1 stop9h 42m
Multiple Airlines
Fri 3/132:15 pm
PNS
- MDW
2 stops9h 36m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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.
Tue 3/1712:45 pm
ORD
- PNS
1 stop8h 29m
Spirit Airlines
Wed 3/182:15 pm
PNS
- ORD
1 stop9h 02m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$217
One-way flights from Chicago to Gulf ShoresSearch for one-way flight options from Chicago to Gulf Shores. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Chicago to Gulf Shores. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Trip.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:30 am
ORD
- PNS
1 stop9h 12m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$63
This Expedia deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1810:44 am
ORD
- PNS
1 stop6h 58m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$66
This Super.com deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1710:44 am
ORD
- PNS
1 stop6h 58m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” 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.
Tue 3/38:30 am
ORD
- PNS
1 stop9h 12m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$71
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:55 pm
MDW
- PNS
Nonstop2h 15m
Southwest
Deal found 2/2![Southwest logo]()
$72
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:44 am
ORD
- PNS
1 stop6h 58m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$72
This Mytrip deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:51 pm
ORD
- PNS
2 stops22h 51m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$76
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:51 pm
ORD
- PNS
2 stops22h 51m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$77
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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.
Fri 3/66:30 pm
ORD
- PNS
1 stop23h 48m
Frontier
Deal found 2/2![Frontier logo]()
$78
This Expedia deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:30 am
MDW
- PNS
1 stop25h 20m
Frontier
Deal found 2/2![Frontier logo]()
$80
This Frontier deal was found by Cheapflights users on 2/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:55 am
ORD
- PNS
1 stop7h 44m
Frontier
Deal found 2/4![Frontier logo]()
$80
This Super.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/910:48 am
ORD
- PNS
1 stop5h 49m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$81
Find flight deals from Chicago to Gulf Shores
Keep the following information in mind while searching for Chicago to Gulf Shores flight deals. Data was last updated February 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Kiwi.com) |
One-way from | $63 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $310 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Gulf Shores 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 February 4, 2026.
Use the filters below to find and compare flights from Chicago to Gulf Shores that are best for you.
Fly from
Chicago
Fly to
Gulf Shores
Route
Depart
Return
Price
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Tue 3/3
6:00 am-9:50 am
1 stop3h 50m
Pensacola
Tue 3/10
5:20 pm-7:35 pm
Nonstop2h 15m
$217
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Wed 3/11
6:07 pm-11:13 pm
1 stop5h 06m
Pensacola
Sun 3/15
6:00 am-9:56 am
1 stop3h 56m
$227
ChicagoPensacola
ORD - PNS
ORDPNS
Chicago O'Hare Intl
Sun 3/8
6:02 pm-8:28 pm
Nonstop2h 26m
Pensacola
Thu 3/12
7:00 am-9:38 am
Nonstop2h 38m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Thu 3/12
6:07 pm-10:04 pm
1 stop3h 57m
Pensacola
Sun 3/15
6:00 am-9:56 am
1 stop3h 56m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Wed 4/1
3:35 pm-8:05 pm
1 stop4h 30m
Pensacola
Wed 4/8
7:40 am-1:30 pm
1 stop5h 50m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Thu 3/12
6:07 pm-10:04 pm
1 stop3h 57m
Pensacola
Tue 3/17
6:00 am-12:02 pm
1 stop6h 02m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Mon 3/9
6:07 pm-10:04 pm
1 stop3h 57m
Pensacola
Tue 3/17
6:00 am-9:56 am
1 stop3h 56m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Wed 3/11
6:00 am-10:06 am
1 stop4h 06m
Pensacola
Tue 3/17
6:00 am-9:56 am
1 stop3h 56m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Thu 3/12
6:07 pm-10:04 pm
1 stop3h 57m
Pensacola
Thu 3/19
6:00 am-9:56 am
1 stop3h 56m
$227
ChicagoPensacola
ORD - PNS
ORDPNS
Chicago O'Hare Intl
Wed 3/11
5:30 am-10:06 am
1 stop4h 36m
Pensacola
Tue 3/17
3:55 pm-9:10 pm
1 stop5h 15m
$227
Showing 1-10 of 41 results
Best time to book a flight from Chicago to Gulf Shores
Have a flexible travel schedule? Discover the best time to fly to Gulf Shores from Chicago with our price prediction graph.
ORD-PNS
MDW-PNS
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 Gulf Shores
CHI-GU9
ORD-PNS
MDW-PNS
How far ahead should I book a flight from Chicago to Gulf Shores?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Gulf Shores. Price data was last updated on January 30, 2026.
The price you pay for your flight from Chicago to Gulf Shores may vary depending on when you book. For the best chance of a lower fare, look to book 62 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago to Gulf Shores?
Currently, July is the cheapest month in which you can book a flight from Chicago to Gulf Shores (average of $81). Flying from Chicago to Gulf Shores in December is currently the most expensive (average of $209). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to GU9?
Find hourly flight availability from Chicago to Gulf Shores. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 4, 2026.
When flying from Chicago to Gulf Shores, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 6% versus a flight in the afternoon.
Weekly flight availability from Chicago to Gulf Shores
Explore weekly flight availability from Chicago to Gulf Shores. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 4, 2026.
The most flights from CHI to GU9 are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Chicago to Gulf Shores?
Reviews of airlines servicing Gulf Shores
Get insights into the airlines that provide service to Gulf Shores. 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 Gulf Shores. Reviews last updated February 4, 2026.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago to Gulf Shores 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
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Entertainment
7.5
Overall
8.0
Comfort
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Chicago to Gulf Shores. 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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Alternative routes for Chicago to Gulf Shores
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Complete your trip
Complete your trip to Gulf Shores by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Chicago to Gulf Shores, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Gulf Shores flights
Browse other Chicago and Gulf Shores flight options. Last updated on February 4, 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 February 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Chicago to Gulf Shores
Discover the top 6 airlines that operate flights from Chicago to Gulf Shores. 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 February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$82 | Average$168 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$116 | Average$210 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$176 | Average$342 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$398 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$392 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$212 | Average$364 | FlexibilityNo cancel fee | On-time63% |