$63 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 3/4. 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
$217
Overall average: $377
Spirit Airlines
Tue 3/17Wed 3/18
ORD - PNS • 1 stop
Cheapest non-stop
$227
Typical prices: $275-$562
United Airlines
Thu 3/5Sun 3/8
ORD - PNS • Non-stop
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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

Tue, Mar 17 - Wed, Mar 18
Spirit Airlines Logo
12:45 pm - 9:14 pm
ORD
-
PNS
8h 29m
1 stop
Spirit Airlines Logo
2:15 pm - 11:17 pm
PNS
-
ORD
9h 02m
1 stop
$217Spirit Airlines
Tue, Mar 3 - Fri, Mar 6
Southwest Logo
2:35 pm - 6:25 pm
MDW
-
PNS
3h 50m
1 stop
Southwest Logo
5:25 pm - 7:40 pm
PNS
-
MDW
2h 15mnonstop
$217Southwest
Sun, Mar 1 - Sun, Mar 8
Multiple Airlines Logo
8:16 pm - 5:42 pm
ORD
-
PNS
21h 26m
2 stops
Multiple Airlines Logo
6:37 pm - 3:28 pm
PNS
-
ORD
20h 51m
1 stop
$218Multiple Airlines
Thu, Feb 12 - Wed, Feb 18
Multiple Airlines Logo
4:16 pm - 6:15 pm
ORD
-
PNS
25h 59m
1 stop
Multiple Airlines Logo
5:20 pm - 11:47 pm
PNS
-
ORD
6h 27m
1 stop
$219Multiple Airlines
Sat, Mar 7 - Sat, Mar 14
Spirit Airlines Logo
8:16 pm - 4:42 pm
ORD
-
PNS
20h 26m
2 stops
Spirit Airlines Logo
7:00 am - 4:56 pm
PNS
-
ORD
9h 56m
1 stop
$220Spirit Airlines
Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
8:00 am - 5:42 pm
MDW
-
PNS
9h 42m
1 stop
Multiple Airlines Logo
6:37 pm - 9:12 pm
PNS
-
MDW
26h 35m
2 stops
$220Multiple Airlines
Sun, Mar 1 - Sun, Mar 8
Spirit Airlines Logo
6:51 pm - 5:42 pm
ORD
-
PNS
22h 51m
2 stops
Spirit Airlines Logo
6:37 pm - 9:13 pm
PNS
-
ORD
26h 36m
2 stops
$221Spirit Airlines
Sun, Mar 8 - Fri, Mar 13
Multiple Airlines Logo
8:00 am - 5:42 pm
MDW
-
PNS
9h 42m
1 stop
Multiple Airlines Logo
2:15 pm - 11:51 pm
PNS
-
MDW
9h 36m
2 stops
$221Multiple Airlines
Sat, Apr 4 - Sat, Apr 11
Southwest Logo
4:55 pm - 7:10 pm
MDW
-
PNS
2h 15mnonstop
Southwest Logo
8:00 am - 2:35 pm
PNS
-
MDW
6h 35m
2 stops
$223Southwest
Fri, Mar 13 - Tue, Mar 17
Delta Logo
6:07 pm - 10:04 pm
MDW
-
PNS
3h 57m
1 stop
Delta Logo
3:55 pm - 10:31 pm
PNS
-
MDW
6h 36m
1 stop
$227Delta
Useful Info

Good to know

Low seasonOctober
Cheapest flight$63
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 14% 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?

    9 direct flights run between Chicago and Orange Beach on a daily basis. On average, there are about 67 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 Sundays 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 $73. Spirit Airlines offered a round-trip connection from $116 and Delta from $176.

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 62 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 February, March and April. The cheapest month to fly is September.

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 4272 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

10.0 ExcellentMeghan, Feb 2026
MCO - DEN
Read more Southwest reviews

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

We loved the steward on the plane. He made the night enjoyable

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

We were on the tarmac waiting for a gate at Logan for 40, minutes. The crew handled it well. Can't blame the airline.

That gate is like a ducking shelter at Newark No where to sit Outlets that don’t work Bathrooms that are dirty

Everything was good. On time, boarding fast, flight attendants friendly.

Great, but seats are terrible. Way too cramped for any human.

Spirit has always and will always stink. Absolute worst airline around.

It was smooth sailing snags we had a really smooth landing and a great flight!

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

All very good except they didn’t load our walker so haven’t gotten it yet

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