$112 Find Cheap Flights from Chicago to Orange Beach

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Orange Beach departing on 8/13. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$298
Typical prices: $395-$247
Multiple Airlines
Wed 10/7Mon 10/12
ORD - PNS • 2 stops
Cheapest non-stop
$349
Southwest
Wed 7/1Wed 7/8
MDW - PNS • Non-stop
Arrival airport
You can't fly directly to Orange Beach. It is served by Pensacola (PNS), located 27.8 miles from Orange Beach.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Orange Beach (CHI-PNS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Orange Beach that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Orange Beach

Wed, Oct 7 - Mon, Oct 12
Multiple Airlines Logo
2:03 pm - 7:38 am
ORD
-
PNS
17h 35m
2 stops
Multiple Airlines Logo
5:30 pm - 1:16 pm
PNS
-
ORD
19h 46m
1 stop
$298Multiple Airlines
Fri, Jul 10 - Tue, Jul 14
Frontier Logo
10:16 am - 4:33 pm
ORD
-
PNS
6h 17m
1 stop
Frontier Logo
3:15 pm - 11:05 pm
PNS
-
ORD
7h 50m
1 stop
$299Frontier
Wed, Jul 1 - Wed, Jul 8
Frontier Logo
9:48 pm - 6:48 pm
ORD
-
PNS
21h 00m
1 stop
Frontier Logo
3:15 pm - 11:05 pm
PNS
-
ORD
7h 50m
1 stop
$301Frontier
Wed, Jul 29 - Wed, Aug 5
Multiple Airlines Logo
5:13 pm - 1:59 pm
ORD
-
PNS
20h 46m
1 stop
Multiple Airlines Logo
12:49 pm - 12:25 pm
PNS
-
ORD
23h 36m
1 stop
$302Multiple Airlines
Wed, Jun 24 - Sat, Jun 27
Frontier Logo
9:48 pm - 6:48 pm
ORD
-
PNS
21h 00m
1 stop
Frontier Logo
7:43 pm - 8:43 pm
PNS
-
ORD
25h 00m
1 stop
$304Frontier
Wed, Jul 15 - Sat, Jul 18
Frontier Logo
9:57 pm - 6:48 pm
ORD
-
PNS
20h 51m
1 stop
Frontier Logo
3:15 pm - 11:05 pm
PNS
-
ORD
7h 50m
1 stop
$307Frontier
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
12:55 pm - 3:05 pm
MDW
-
PNS
2h 10mnonstop
Southwest Logo
3:45 pm - 6:00 pm
PNS
-
MDW
2h 15mnonstop
$349Southwest
Tue, Jul 7 - Sat, Jul 11
Southwest Logo
12:55 pm - 3:05 pm
MDW
-
PNS
2h 10mnonstop
Southwest Logo
3:50 pm - 6:05 pm
PNS
-
MDW
2h 15mnonstop
$352Southwest
Thu, Jun 25 - Tue, Jun 30
Southwest Logo
7:45 am - 10:00 am
MDW
-
PNS
2h 15mnonstop
Southwest Logo
3:45 pm - 6:00 pm
PNS
-
MDW
2h 15mnonstop
$353Southwest
Sun, May 24 - Sun, May 24
Southwest Logo
8:50 am - 11:05 am
MDW
-
PNS
2h 15mnonstop
Southwest Logo
5:05 pm - 7:20 pm
PNS
-
MDW
2h 15mnonstop
$355Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$112
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago O'Hare Airport to Pensacola

When to book flights from Chicago to Orange Beach

Are your dates flexible? Find out the best times to travel from Chicago to Orange Beach based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Orange Beach

  • Which airports will I be using when flying from Chicago to Orange Beach?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Orange Beach does not have its own airport so you’ll be flying into nearby Pensacola airport, which is 27.8 mi away.

  • How long does a flight from Chicago to Orange Beach take?

    Direct flights cover the 788 miles separating Chicago and Orange Beach in about 2h 10m.

  • How many flights are there between Chicago and Orange Beach?

    5 direct flights run between Chicago and Orange Beach on a daily basis. On average, there are about 37 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Orange Beach?

    Consider leaving on a Monday and avoid Wednesdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Saturdays.

  • How does KAYAK find such low prices on flights from Chicago to Orange Beach?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Orange Beach.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Orange Beach?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Orange Beach from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Orange Beach?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Orange Beach with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Orange Beach?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Orange Beach from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Orange Beach?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Orange Beach found on KAYAK was with Spirit Airlines for $81. Delta offered a round-trip connection from $128 and Spirit Airlines from $183.

Top tips for finding cheap flights from Chicago to Orange Beach

  • There is no airport in Orange Beach. Instead, you’ll be flying into Pensacola Airport when flying between Chicago and Orange Beach.
  • The cheapest flight from Chicago to Orange Beach was found 70 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be April, May and June. The cheapest month to fly is November.

Reviews of the top 5 airlines serving Chicago to Orange Beach

 
Need help choosing which airline to fly with from Chicago to Orange Beach? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4284 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

10.0 ExcellentAnonymous, May 2026
PDX - OAK
Read more Southwest reviews

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

It would have been better IF IT HAD NOT BEEN CANCELED!!!!

The airline cancel mi flight, lost a lot of money!!!

They cancelled our flight. 2 hours before we were supposed to take off and offered us nothing! We got our money back and that was it. No other flight to get to our cruise no working with another airline or with us to get there. Terrible customer service, no apology.

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

Flight was delayed for 12 h. They should stop overlooking flights.

All of our flights were canceled, though every other airline was flying out and in

it was terrible. flight was cancelled hours before the flight without a given reason and no other booking available .

Everything you need to know for your flight from Chicago to Orange Beach

Complete your trip to Orange Beach with a hotel stay or car rental