$81 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 8/17. 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.
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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

Mon, Aug 18 - Sat, Aug 23
Spirit Airlines Logo
5:05 am - 3:57 pmORD-PNS
10h 52m1 stop
Spirit Airlines Logo
9:14 am - 7:07 pmPNS-ORD
9h 53m1 stop
$168Spirit Airlines
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Tue, Aug 12 - Fri, Aug 15
Spirit Airlines Logo
4:36 pm - 10:41 pmORD-PNS
6h 05m1 stop
Spirit Airlines Logo
4:52 pm - 11:59 pmPNS-ORD
7h 07m1 stop
$169Spirit Airlines
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Mon, Aug 18 - Sat, Aug 23
Spirit Airlines Logo
5:05 am - 3:57 pmORD-PNS
10h 52m1 stop
Spirit Airlines Logo
9:14 am - 7:07 pmPNS-ORD
9h 53m1 stop
$171Spirit Airlines
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Thu, Sep 25 - Tue, Sep 30
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
$173Spirit Airlines
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Sat, Aug 23 - Sat, Aug 30
Southwest Logo
8:20 am - 10:30 amMDW-PNS
2h 10mnonstop
Southwest Logo
4:45 pm - 6:55 pmPNS-MDW
2h 10mnonstop
$217Southwest
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Wed, Nov 5 - Tue, Nov 11
American Airlines Logo
10:30 am - 1:00 pmORD-PNS
2h 30mnonstop
American Airlines Logo
1:32 pm - 4:11 pmPNS-ORD
2h 39mnonstop
$217American Airlines
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Sat, Aug 23 - Sat, Aug 30
Southwest Logo
10:25 am - 3:05 pmMDW-PNS
4h 40m1 stop
Southwest Logo
4:45 pm - 6:55 pmPNS-MDW
2h 10mnonstop
$227Southwest
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Sat, Aug 23 - Sat, Aug 30
Delta Logo
4:25 pm - 9:46 pmMDW-PNS
5h 21m1 stop
Delta Logo
9:23 am - 3:28 pmPNS-MDW
6h 05m1 stop
$229Delta
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Wed, Sep 10 - Wed, Sep 17
Delta Logo
7:05 am - 1:08 pmORD-PNS
6h 03m1 stop
Delta Logo
9:22 am - 2:33 pmPNS-ORD
5h 11m1 stop
$237Delta
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Thu, Sep 25 - Tue, Sep 30
United Airlines Logo
10:50 am - 1:15 pmORD-PNS
2h 25mnonstop
United Airlines Logo
2:17 pm - 4:54 pmPNS-ORD
2h 37mnonstop
$240United Airlines
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Good to know

Low seasonJanuary
Cheapest flight$81
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 12% 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?

    2 direct flights run between Chicago and Orange Beach on a daily basis. On average, there are about 15 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 Wednesdays and the most expensive ones on Thursdays.

  • 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. Spirit Airlines offered a round-trip connection from $168 and American Airlines from $217.

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 84 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 4241 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

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.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

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.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Had a issue with catching flight due to airline, was unable to board flight

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

We sat on the tarmac for an hour waiting for a gate to deplane.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

Everything was fine, but there was no food or entertainment, so I didn’t know how to rate that.

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

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