$91 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 10/19. 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

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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

Tue, Oct 14 - Fri, Oct 17
United Airlines Logo
10:50 am - 1:15 pmORD-PNS
2h 25mnonstop
United Airlines Logo
2:17 pm - 4:54 pmPNS-ORD
2h 37mnonstop
$203United Airlines
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Wed, Oct 1 - Sat, Oct 4
Spirit Airlines Logo
6:30 am - 6:10 pmORD-PNS
11h 40m1 stop
Spirit Airlines Logo
4:44 pm - 10:48 pmPNS-ORD
6h 04m1 stop
$205Spirit Airlines
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Fri, Oct 3 - Sun, Oct 5
Frontier Logo
6:00 am - 4:26 pmORD-PNS
10h 26m1 stop
Frontier Logo
5:21 pm - 11:59 pmPNS-ORD
6h 38m1 stop
$215Frontier
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Tue, Oct 14 - Wed, Oct 22
Southwest Logo
8:40 am - 3:30 pmMDW-PNS
6h 50m1 stop
Southwest Logo
1:25 pm - 7:05 pmPNS-MDW
5h 40m1 stop
$217Southwest
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Tue, Oct 21 - Wed, Oct 29
Delta Logo
1:26 pm - 7:17 pmORD-PNS
5h 51m1 stop
Delta Logo
7:00 am - 12:16 pmPNS-ORD
5h 16m1 stop
$217Delta
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Wed, Nov 19 - Wed, Nov 26
Southwest Logo
10:50 am - 3:35 pmMDW-PNS
4h 45m1 stop
Southwest Logo
9:50 am - 4:50 pmPNS-MDW
7h 00m1 stop
$218Southwest
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Wed, Nov 19 - Wed, Nov 26
Delta Logo
5:32 am - 10:41 amORD-PNS
5h 09m1 stop
Delta Logo
7:09 pm - 12:02 amPNS-ORD
4h 53m1 stop
$223Delta
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Wed, Nov 5 - Wed, Nov 19
American Airlines Logo
9:45 am - 4:07 pmORD-PNS
6h 22m1 stop
American Airlines Logo
1:32 pm - 4:11 pmPNS-ORD
2h 39mnonstop
$234American Airlines
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Wed, Nov 5 - Mon, Nov 10
American Airlines Logo
10:30 am - 1:00 pmORD-PNS
2h 30mnonstop
American Airlines Logo
1:01 pm - 3:39 pmPNS-ORD
2h 38mnonstop
$237American Airlines
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Mon, Sep 29 - Fri, Oct 3
Frontier Logo
6:00 am - 4:26 pmORD-PNS
10h 26m1 stop
Frontier Logo
5:21 pm - 11:27 amPNS-ORD
18h 06m2 stops
$238Frontier
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Good to know

Low seasonDecember
Cheapest flight$91
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly with an average 15% 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 25m.

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

    3 direct flights run between Chicago and Orange Beach on a daily basis. On average, there are about 21 departures each week.

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

    Consider leaving on a Tuesday 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 Sundays.

  • 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 $91. United Airlines offered a round-trip connection from $203 and Spirit Airlines from $205.

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 16 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 November, December and January. The cheapest month to fly is January.

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.
8.0
SouthwestOverall score based on 4242 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

The staff and the boarding procedure were all amazing . The one flight was not equipped with WIFI which now adays seems odd. All in all the experience was good

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

Spirit rescheduled a 4:30 PM flight to 8:52 AM. That's ridiculous and borderline fraud.

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No Tumberlence smooth flight. Try to change the menu on Snacks.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The terminal crew is so rude cabin crew is extremely rude flight is very good

Spirit is low fare air line. Food also cost you. No free food.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

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

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