$64+ Cheap flights from Chicago (CHI) to Orange Beach, 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PNS
Feb 28 — Mar 71
1 adult, Economy
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Find cheap flights from Chicago to Orange Beach 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 Orange Beach 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 Orange Beach
Cheapest flights from Chicago to Orange BeachExplore the most affordable flight options available from Chicago to Orange Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.
Explore the most affordable flight options available from Chicago to Orange Beach. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.
This CheapOair deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” 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.
Sat 2/710:48 am
ORD
- PNS
1 stop5h 49m
Spirit Airlines
Sat 2/145:20 pm
PNS
- ORD
1 stop6h 27m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” 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.
Wed 2/257:00 am
MDW
- PNS
2 stops34h 42m
Multiple Airlines
Wed 3/46:37 pm
PNS
- MDW
1 stop19h 49m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” 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 3/138:41 pm
ORD
- PNS
2 stops24h 33m
Multiple Airlines
Wed 3/187:00 am
PNS
- ORD
1 stop16h 38m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$216
This Mytrip deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” 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.
Fri 3/65:58 pm
ORD
- PNS
2 stops23h 44m
Spirit Airlines
Mon 3/95:20 pm
PNS
- ORD
1 stop6h 27m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” 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 3/46:00 am
MDW
- PNS
1 stop3h 50m
Southwest
Tue 3/105:20 pm
PNS
- MDW
Nonstop2h 15m
Southwest
Deal found 1/27![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” 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 2/2310:44 am
ORD
- PNS
1 stop6h 58m
Spirit Airlines
Tue 2/246:37 pm
PNS
- ORD
2 stops16h 45m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” 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 2/209:07 pm
ORD
- PNS
1 stop20h 35m
Multiple Airlines
Tue 2/246:37 pm
PNS
- ORD
2 stops16h 45m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” 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 2/2310:44 am
ORD
- PNS
1 stop6h 58m
Multiple Airlines
Sat 2/2811:18 am
PNS
- ORD
2 stops13h 22m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$220
This Mytrip deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” 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.
Thu 3/510:44 am
ORD
- PNS
1 stop6h 58m
Spirit Airlines
Tue 3/106:37 pm
PNS
- ORD
2 stops24h 34m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” 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 2/227:30 am
MDW
- PNS
2 stops32h 24m
Multiple Airlines
Fri 2/276:37 pm
PNS
- MDW
1 stop20h 18m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” 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 4/99:30 am
ORD
- PNS
1 stop11h 44m
Multiple Airlines
Tue 4/147:00 am
PNS
- ORD
2 stops14h 17m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$222
This Cheapflightsfares deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” 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.
Fri 5/85:15 am
ORD
- PNS
1 stop7h 37m
Spirit Airlines
Mon 5/111:47 pm
PNS
- ORD
1 stop9h 54m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$223
Find flight deals from Chicago to Orange Beach
Keep the following information in mind while searching for Chicago to Orange Beach flight deals. Data was last updated January 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $215 (Kiwi.com) |
One-way from | $64 (Trip.com) |
Popular in | March |
Cheapest in | September |
Average price | $353 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Orange Beach 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 January 29, 2026.
Use the filters below to find and compare flights from Chicago to Orange Beach that are best for you.
Fly from
Chicago
Fly to
Orange Beach
Route
Depart
Return
Price
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sun 4/19
6:00 am-10:02 am
1 stop4h 02m
Pensacola
Wed 4/22
6:00 am-9:56 am
1 stop3h 56m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Wed 2/18
6:40 pm-11:11 pm
1 stop4h 31m
Pensacola
Tue 2/24
6:00 am-11:59 am
1 stop5h 59m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Mon 2/23
12:45 pm-6:19 pm
1 stop5h 34m
Pensacola
Tue 2/24
6:00 am-9:54 am
1 stop3h 54m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sun 2/22
6:00 am-10:31 am
1 stop4h 31m
Pensacola
Tue 2/24
4:04 pm-10:33 pm
1 stop6h 29m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sun 2/22
6:00 am-12:30 pm
1 stop6h 30m
Pensacola
Wed 2/25
6:00 am-11:59 am
1 stop5h 59m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Wed 2/25
6:00 am-10:31 am
1 stop4h 31m
Pensacola
Wed 2/25
5:48 pm-10:31 pm
1 stop4h 43m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Wed 3/11
6:00 am-10:06 am
1 stop4h 06m
Pensacola
Sun 3/15
6:00 am-9:56 am
1 stop3h 56m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Sun 3/8
6:00 am-10:06 am
1 stop4h 06m
Pensacola
Wed 3/11
6:00 am-9:56 am
1 stop3h 56m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Tue 2/24
6:00 am-12:30 pm
1 stop6h 30m
Pensacola
Wed 2/25
6:00 am-9:54 am
1 stop3h 54m
$227
ChicagoPensacola
MDW - PNS
MDWPNS
Chicago Midway
Mon 3/2
10:49 am-2:54 pm
1 stop4h 05m
Pensacola
Thu 3/5
6:00 am-9:54 am
1 stop3h 54m
$227
Showing 1-10 of 48 results
Best time to book a flight from Chicago to Orange Beach
Have a flexible travel schedule? Discover the best time to fly to Orange Beach from Chicago with our price prediction graph.
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 Orange Beach
How far ahead should I book a flight from Chicago to Orange Beach?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Orange Beach. Price data was last updated on January 23, 2026.
The best time to book flights from Chicago to Orange Beach is 62 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Chicago to Orange Beach?
Currently, July is the cheapest month in which you can book a flight from Chicago to Orange Beach (average of $81). Flying from Chicago to Orange Beach in August is currently the most expensive (average of $217). 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 OB9?
Find hourly flight availability from Chicago to Orange Beach. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 11% on flights from Chicago to Orange Beach by exploring options for tickets in the evening.
Weekly flight availability from Chicago to Orange Beach
Explore weekly flight availability from Chicago to Orange Beach. 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 January 29, 2026.
The most flights from CHI to OB9 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 Orange Beach?
Reviews of airlines servicing Orange Beach
Get insights into the airlines that provide service to Orange Beach. 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 Orange Beach. Reviews last updated January 29, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Chicago to Orange Beach. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Overall
8.0
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 Orange Beach. 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 Orange Beach
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from Chicago to Orange Beach
Discover the top 6 airlines that operate flights from Chicago to Orange Beach. 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 January 29, 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$154 | Average$347 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$209 | Average$397 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$209 | Average$392 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$212 | Average$364 | FlexibilityNo cancel fee | On-time63% |