$41 Find Cheap Flights to Pleasant Prairie

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Pleasant Prairie departing on 7/9. 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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Cheap Flights to Pleasant Prairie

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Pleasant Prairie 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 to Pleasant Prairie

Fri, Jul 4 - Tue, Jul 8
Spirit Airlines Logo
5:00 am - 6:37 amEWR-ORD
2h 37mnonstop
Spirit Airlines Logo
9:28 pm - 12:46 amORD-EWR
2h 18mnonstop
$85Spirit Airlines
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Fri, Jul 4 - Tue, Jul 8
Spirit Airlines Logo
5:00 am - 6:37 amEWR-ORD
2h 37mnonstop
Spirit Airlines Logo
9:28 pm - 12:46 amORD-EWR
2h 18mnonstop
$87Spirit Airlines
Find Deal
Mon, Aug 18 - Tue, Aug 19
Frontier Logo
8:54 am - 11:37 amDFW-ORD
2h 43mnonstop
Frontier Logo
5:27 pm - 8:16 pmORD-DFW
2h 49mnonstop
$117Frontier
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Sat, Aug 16 - Mon, Aug 18
Frontier Logo
1:30 pm - 4:14 pmDFW-ORD
2h 44mnonstop
Frontier Logo
5:20 am - 7:58 amORD-DFW
2h 38mnonstop
$122Frontier
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Wed, Aug 13 - Mon, Aug 18
United Airlines Logo
6:07 am - 8:05 amBOS-ORD
2h 58mnonstop
United Airlines Logo
6:00 am - 9:26 amORD-BOS
2h 26mnonstop
$125United Airlines
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Wed, Aug 13 - Wed, Aug 13
American Airlines Logo
6:00 am - 7:25 amPHL-ORD
2h 25mnonstop
American Airlines Logo
10:22 am - 1:26 pmORD-PHL
2h 04mnonstop
$134American Airlines
Find Deal
Wed, Jul 9 - Sat, Jul 12
United Airlines Logo
6:07 am - 8:05 amBOS-ORD
2h 58mnonstop
United Airlines Logo
7:45 pm - 11:12 pmORD-BOS
2h 27mnonstop
$137United Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
American Airlines Logo
6:48 pm - 8:34 pmLGA-ORD
2h 46mnonstop
American Airlines Logo
2:03 pm - 5:15 pmORD-LGA
2h 12mnonstop
$140American Airlines
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Tue, Jul 15 - Fri, Jul 18
Delta Logo
7:20 am - 9:18 amBOS-ORD
2h 58mnonstop
Delta Logo
7:10 pm - 10:50 pmORD-BOS
2h 40mnonstop
$147Delta
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Tue, Sep 2 - Wed, Sep 10
Delta Logo
7:29 pm - 9:47 pmJFK-ORD
3h 18mnonstop
Delta Logo
1:25 pm - 5:00 pmORD-JFK
2h 35mnonstop
$152Delta
Find Deal
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Good to know - Book Cheap Pleasant Prairie Plane Tickets

Low seasonJanuary
High seasonJuly
Cheapest flight$41
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Los Angeles to Chicago O'Hare Airport

Flights to Pleasant Prairie: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Pleasant Prairie 
DouglasFlew with American AirlinesHSV-ORDJun 2025
Check your app for delay notices. This notice did come out early in the morning - I failed to check it. Checking it could have saved 4 hours at the airport
Verified travelerFlew with British AirwaysDSM-ORDJun 2025
Make sure your luggage receipts have the ID numbers on them
Verified travelerFlew with Air CanadaJAX-ORDApr 2025
Chicago is a huge airport, wear comfortable shoes if you're looking to make a connection. It might be a 15 minute speed walk. Jacksonville is a little more compact and easier to navigate. Lots of food and beverage options in each.
StaceyFlew with American AirlinesPHX-ORDFeb 2025
Don’t be that person who holds up the plane because of your carry on. Whether putting in over bin (able to lift it on your own) or refusing to not listen when space is full and need to check it.
Verified travelerFlew with United AirlinesBTV-ORDDec 2024
Get to know the airport plan in advance because it is a confusing one.
valerieFlew with Air CanadaSTL-ORDJan 2025
Usually it is unreliable - always leave lots of time for connection.
StephenFlew with United AirlinesEWR-ORDJan 2025
Don't bring a carry on roller bag. It won't fit. They will gate check it. It will take forever.
RodFlew with United AirlinesSAN-ORDSep 2024
Yes! Don’t reserve a flight with less than 1 1/2 hour connection time or you have a good possibility of missing your connection.
GeraldFlew with Alaska AirlinesSFO-ORDOct 2024
Book a flight as early in the day as possible to avoid incoming flight delays.
AdamFlew with SouthwestDEN-ORDOct 2024
Arriving T5 at ORD on Southwest is often a LONG walk, with no moving walkways going out, to baggage claim / pickup.
DinaFlew with United AirlinesHSV-ORDNov 2024
Be prepared for delays and plan to check your luggage. Overhead bins are ⅓ the size of a typical bin.
KimFlew with American AirlinesSNA-ORDNov 2024
Bring extra foods and buy extra drinks bring your meds
LeoFlew with United AirlinesCLT-ORDJun 2024
Get precheck TSA if you’re flying in early morning. Get a seat on the right side of the plane if you want to see sunrise.
Verified travelerFlew with American AirlinesPHL-ORDJul 2024
Fly out the night before you have anything to do in Chicago so you don’t get delayed and miss out on plans
JenniferFlew with American AirlinesCLT-ORDJul 2024
Both the Charlotte and O'Hare airports are large and well organized. Wear you comfy walking shoes and enjoy the journey!
CameonFlew with FrontierSLC-ORDJul 2024
Fly Delta! Book directly through the airline, not a second booking party.
GailFlew with JetBlueBOS-ORDJul 2024
Prepare for a long wait after you actually touch down. Ohare Airport is HUGE and you can taxi for a long time.
Verified travelerFlew with United AirlinesSEA-ORDJul 2024
Budget if you’re planning on shopping for meals or souvenirs at Sea-Tac, it’s not cheap.
ShirleyFlew with United AirlinesLAX-ORDMay 2024
Check-in using the United AirLines app to access your boarding pass. Arrive at least two hours early at LAX airport.
MichelleFlew with United AirlinesMBS-ORDApr 2024
Bring water on board and charge your devices in advance.
EllenFlew with United AirlinesGSP-ORDMay 2024
Greenville airport is small, getting through security won't take too long (particularly if you have Precheck). Be prepared to walk for 10-15 minutes from your arrival gate in O'Hare to your next departure gate, if you have one. Sometimes those gates are really close together, but my experience is that they are typically farther apart and require a solid walk.
Verified travelerFlew with SouthwestLAS-ORDMay 2024
Leave plenty of time to get your bag in Chicago if you check one. Took 45 minutes to get my bag this time.
Verified travelerFlew with Alaska AirlinesSDF-ORDApr 2024
If flight gets delayed. Be sure to ask the airlines you traveled with, to rebook the next available flight immediately.
RickyFlew with Spirit AirlinesDFW-ORDMar 2024
Uber pickup is in terminal 2 doors 2D/2E not available in terminal 1
KariFlew with British AirwaysLSE-ORDMay 2024
Ask for assistance. Chicago is huge airport 🛫 and can get lost easy.
yvgeniFlew with United AirlinesEWR-ORDJan 2024
Check the weather before flying , and don’t rely on getting on time to your destination
BrianFlew with United AirlinesDEN-ORDJan 2024
Big airport. Make sure you have enough time between flights for rest, eating, etc…

FAQs - booking Pleasant Prairie flights

  • How long is the flight to Pleasant Prairie?

    Flights from Dallas2h 35m
    Flights from New York2h 25m
    Flights from San Francisco4h 30m
    Flights from Boston2h 42m
    Flights from Los Angeles4h 19m
  • What is the cheapest flight to Chicago O'Hare Airport?

    In the last 3 days, the cheapest flight deal to Chicago O'Hare Airport was found on the route from Los Angeles, at $85 return. The most popular connection is from New York to Chicago O'Hare Airport and KAYAK users have found round-trip deals for as low as $87 in the last 3 days.

  • Which airlines fly to Chicago O'Hare Airport?

    Many airlines fly to Chicago O'Hare Airport, the most common ones being United Airlines, American Airlines, and Delta. See the amount of flights per week for popular airlines flying to Chicago O'Hare Airport.

  • How to fly to Pleasant Prairie?

    You cannot fly directly to Pleasant Prairie. KAYAK recommends you fly to Chicago O'Hare Intl (ORD) (39.62 miles from Pleasant Prairie). From there you can rent a car or get a taxi.

  • What airports are near Pleasant Prairie?

    The closest airport is Milwaukee-Mitchell (MKE) (27.24 mi). Other nearby airports are Chicago O'Hare Intl (ORD) (39.62 mi), Chicago All airports (CHI) (48.68 mi) or Chicago Midway (MDW) (53.77 mi). KAYAK recommends you fly to Chicago O'Hare Intl.

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    Chicago O'Hare Intl Airport is 16 miles from the center of Chicago.

  • How does KAYAK find such low prices on flights to Pleasant Prairie?

    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 to Pleasant Prairie.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Pleasant Prairie?

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

  • What is the Hacker Fare option on flights to Pleasant Prairie?

    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 Pleasant Prairie with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Pleasant Prairie?

    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 Pleasant Prairie up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Pleasant Prairie

  • There is no major airport in Pleasant Prairie. It is instead served by Chicago O'Hare Intl Airport.
  • Looking for cheap airfare to Pleasant Prairie? 25% of our users found round-trip tickets to Pleasant Prairie for the following prices or less: From Boston $342, from Los Angeles $599, from Miami $762
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Pleasant Prairie flight deals.

Reviews of the top 5 airlines flying to Pleasant Prairie

 
Need help choosing which airline to fly with from the United States to Pleasant Prairie? 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
DeltaOverall score based on 7964 reviews
7.3Food
8.5Crew
7.9Comfort
8.2Boarding
7.9Entertainment
Airline reviews

I like for how they process during check in. It was very smoothly.

10.0 ExcellentAbdulla, Jun 2025CMH - JFK
Read more Delta reviews

I like for how they process during check in. It was very smoothly.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

Gate agent did not hold flight for connection, provided no assistance to get new flight

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

United airlines, mediocre at best. No issues , nothing great . Worked for me

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

It was absolutely awesome. The crew was welcoming to all, not just the first class. They were full of energy. The in-cabin music was an excellent choice, not boring like most airlines. We were ready for takeoff ahead of time. Pilots were great. Smooth takeoff and landing. The plane was beautiful and nicely cleaned. This was truly a fantastic flight. I fly Delta and American all the time. I was apprehensive about Spirit. I will definitely be looking for Spirit first. Thanks for a great experience.

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Spirit gets you there; it's no worse than any other aircraft, all things considered. (It's not like everyone else is such a hero). But - holy moses - do they nickel and dime you to absolutely every nickel - I was really expecting to have to pay to use the bathroom. And when the captain comes on with a 5 minute sales pitch about getting "points", that was like something on Bizarro world. Other than that, everyone else was professional and worked hard to get us from point A to point B. I'm not loving all the "self-service" stuff but there it is - just when the machines don't work you don't have anyone to talk to.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

We had to wait in line over an hour just to check our bags. It's a good thing we were so early to the airport. Only one clerk was working and the line was around the corner and down the hall. No good. I felt bad for her. Not sure how she kept her sanity with all the upset people. Then we get to our gate and there is no seating. Everyone was standing. Then I realize it is not a gate at all, we still have to be shuttled to our airplane. Ugh. Then we were late taking off and missed a window of opportunity before the airport runways were shut down for some reason. (not frontier's fault the runway shut down.) The seats on the airline are crammed and there is no cushion. Never had a tighter seating arrangement while flying. My 6' 4" husband was absolutely miserable the whole time with knees digging in to the seat in front of him. You think you are getting a good deal on a ticket, and then wham! I had to pay 75 dollars for our checked bags and 75 dollars for a carry on. No other airline does that!!! And also, there is a 40 pound weight limit on checked bags... Would have been cheaper flying with another airline, and I would have at least gotten a snack and drink. Was thankful for the tiny cup of water at least.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

They canceled flight. Hard to believe there was even a plane incoming for us to get on

The worst. We never made our connection and they did absolutely nothing to help us at the airport.

Our flight was cancelled. They could do nothing to help us get another flight that was timely. Because the first leg was cancelled we were unable to get to our connection. We had to book on an entirely different airline for today. So we spent more money, lost a day of vacation and will never fly Frontier again, so the 'we are sorry, here is $100 credit' is a joke since we won't be flying on Frontier.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. The flight was delayed due to an attendant forgetting to come to work. On the flight no drinks were offered only for purchase meals.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. On the flight no drinks were offered only for purchase meals.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

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