$31 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 5/28. 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 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.

Recent round-trip flight deals to Pleasant Prairie

KAYAK's recommended round-trip deals from the most popular airlines that fly to Pleasant Prairie.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
5:55 am - 7:27 amEWR-ORD
2h 32mnonstop
Spirit Airlines Logo
9:08 pm - 12:29 amORD-EWR
2h 21mnonstop
$72Spirit Airlines
Find Deal
Wed, May 28 - Wed, Jun 4
Spirit Airlines Logo
6:30 pm - 8:07 pmLGA-ORD
2h 37mnonstop
Spirit Airlines Logo
5:51 am - 9:00 amORD-LGA
2h 09mnonstop
$74Spirit Airlines
Find Deal
Wed, May 28 - Wed, Jun 4
Frontier Logo
9:05 pm - 11:49 pmDFW-ORD
2h 44mnonstop
Frontier Logo
5:19 pm - 8:15 pmORD-DFW
2h 56mnonstop
$100Frontier
Find Deal
Fri, Jun 13 - Fri, Jun 20
Frontier Logo
9:05 pm - 11:49 pmDFW-ORD
2h 44mnonstop
Frontier Logo
5:19 pm - 8:15 pmORD-DFW
2h 56mnonstop
$101Frontier
Find Deal
Fri, Jun 13 - Fri, Jun 20
American Airlines Logo
2:08 pm - 4:03 pmBOS-ORD
2h 55mnonstop
American Airlines Logo
8:40 pm - 12:20 amORD-BOS
2h 40mnonstop
$118American Airlines
Find Deal
Sat, Jun 7 - Tue, Jun 10
United Airlines Logo
6:59 pm - 11:37 pmBOS-ORD
5h 38m1 stop
United Airlines Logo
7:30 am - 10:57 amORD-BOS
2h 27mnonstop
$123United Airlines
Find Deal
Tue, Jul 1 - Tue, Jul 8
United Airlines Logo
7:45 am - 9:43 amBOS-ORD
2h 58mnonstop
United Airlines Logo
7:54 pm - 11:21 pmORD-BOS
2h 27mnonstop
$134United Airlines
Find Deal
Sun, May 25 - Wed, May 28
Delta Logo
11:00 am - 12:48 pmJFK-ORD
2h 48mnonstop
Delta Logo
6:18 pm - 10:00 pmORD-JFK
2h 42mnonstop
$137Delta
Find Deal
Tue, May 13 - Tue, May 13
Delta Logo
7:15 am - 8:56 amLGA-ORD
2h 41mnonstop
Delta Logo
8:15 pm - 11:40 pmORD-LGA
2h 25mnonstop
$137Delta
Find Deal
Tue, May 20 - Wed, May 21
American Airlines Logo
9:00 am - 11:09 amJFK-ORD
3h 09mnonstop
American Airlines Logo
4:44 pm - 8:00 pmORD-JFK
2h 16mnonstop
$138American Airlines
Find Deal
Tue, May 13 - Wed, May 14
Useful Info

Good to know - Book Cheap Pleasant Prairie Plane Tickets

Low seasonJanuary
High seasonJuly
Cheapest flight$31
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Newark Liberty Airport 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 
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.
JaneFlew with Spirit AirlinesTPA-ORDApr 2025
Tampa Airport is actually quite nice. I can't comment on Chicago since that trip didn't actually happen. As per airlines, I think Allegiant actually does a pretty good job for being a low-cost carrier. JetBlue is nice too.
Verified travelerFlew with United AirlinesBTV-ORDDec 2024
Get to know the airport plan in advance because it is a confusing one.
DinaFlew with United AirlinesSFO-ORDDec 2024
Choose an airline that will accommodate your needs
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.
valerieFlew with Air CanadaSTL-ORDJan 2025
Usually it is unreliable - always leave lots of time for connection.
JaevesFlew with DeltaMSP-ORDDec 2024
Stay longer in Minneapolis airport because Chicago is a nightmare.
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.
Verified travelerFlew with Alaska AirlinesSEA-ORDOct 2024
Alaska airline has best boarding and baggage policy.
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.
Verified travelerFlew with Spirit AirlinesFLL-ORDOct 2024
Please leave on time. Arrive on time and don’t make people wait almost an hour to off board.
ShirleyFlew with Alaska AirlinesSEA-ORDJun 2024
I generally fly United or Delta out of South Bend, IN into Seattle or wherever I'm going. I have no issues with Alaska. I only use Alaska when flying with my family from the Seattle area back to Chicago O'Hare and then we drive to SW Michigan where I live. Alaska Airlines has a beautiful new terminal at SeaTac as well. A good airline. I do like planes that have screens on the back of the seats.
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.
DonFlew with American AirlinesSFO-ORDJun 2024
United offers the best service from SFO to ORD. Great capacity and several redundant flights in the event of a cancellation or delay.
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!
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.
CameonFlew with FrontierSLC-ORDJul 2024
Fly Delta! Book directly through the airline, not a second booking party.
Verified travelerFlew with Alaska AirlinesSEA-ORDJun 2024
Bring books and earplugs for the four hour flight and enjoy Chicago!
MelanieFlew with United AirlinesBUF-ORDAug 2024
I was pleased with United's service, staff, efficiency.
SkyFlew with American AirlinesDFW-ORDJun 2024
AA is usually decent, maybe because I have to fly budget airlines. To Chicago from Dallas was good. The flight after being delayed a day soured the trip, of course. But quick flights intercontinentally are well enough.
Verified travelerFlew with LufthansaPHX-ORDJun 2024
I like United Airlines company, but more room for improvement
Verified travelerFlew with Alaska AirlinesPDX-ORDJun 2024
Alaska Airlines was the best with baggage policies, seat assignments, boarding, cleanliness, communication, and overall satisfaction. Spirit is inexpensive but is extremely uncomfortable and very strict on baggage policies and has a lot of additional costs. The check in through spirit was troublesome and complicated. The lady wasn’t very welcoming in help either!
JamesFlew with United AirlinesRIC-ORDJun 2024
If you can, go to DCA because no one but the absolute worst airlines bother going to Richmond. And I don't see this changing.
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.
MarkFlew with American AirlinesPHL-ORDJun 2024
Just say “no” to PHL and ORD. They are both a nightmare for delays and missed connections.
TravisFlew with United AirlinesHNL-ORDAug 2024
If you can afford another airline, I'd avoid United.
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 Spirit AirlinesRSW-ORDApr 2024
Fly with Southwest, they are the best, good customer service, flexible schedule, no extra charge for luggage, several flights a day, comparable price. If you don't want to be stranded, DO NOT fly on Spirit!
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.
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.
KariFlew with British AirwaysLSE-ORDMay 2024
Ask for assistance. Chicago is huge airport 🛫 and can get lost easy.
MichelleFlew with United AirlinesMBS-ORDApr 2024
Bring water on board and charge your devices in advance.
Verified travelerFlew with American AirlinesSTL-ORDMay 2024
The flight from STL to Chicago was good
JanetFlew with American AirlinesAZO-ORDApr 2024
Wish I knew they’d take my carryon to store with luggage when I got into plane
RickyFlew with Spirit AirlinesDFW-ORDMar 2024
Uber pickup is in terminal 2 doors 2D/2E not available in terminal 1
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.
ChristineFlew with American AirlinesASE-ORDDec 2023
It’s a small airport so you’re only getting commuter jets. But it’s very nice.
BrianFlew with United AirlinesDEN-ORDJan 2024
Big airport. Make sure you have enough time between flights for rest, eating, etc…
Verified travelerFlew with Air CanadaALB-ORDFeb 2024
Be prepared, travel with just what u truly need. Be considerate of others
yvgeniFlew with United AirlinesEWR-ORDJan 2024
Check the weather before flying , and don’t rely on getting on time to your destination

FAQs - booking Pleasant Prairie flights

  • How long is the flight to Pleasant Prairie?

    Flights from New York2h 25m
    Flights from San Francisco4h 35m
    Flights from Minneapolis1h 38m
    Flights from Boston2h 43m
    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 Newark, at $72 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 $74 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 $389, from Los Angeles $615, from Miami $787
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Pleasant Prairie flight deals.

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 7936 reviews
8.2Boarding
7.3Food
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

8.0 ExcellentFredrick, Apr 2025GSO - DTW
Read more Delta reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

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

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

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.

leg space better than expected. two washrooms for one plane isn't enough.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

Several delays. Next flight was worse. Did not arrive home until 2am PT

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

First world problems, but still… We were seated in first class and asked for a cocktail on a very short, 50 minute flight. After our drink order was taken, a half hour went by, and we noticed that every other person in the small plane had been served except for us. We got up to ask about it, the drinks finally came, then were taken away three minutes later since the flight was so short. Really strange situation, on the other hand, we were in Utah.

We missed our flight. The boarding pass had the wrong gate and by the time we received the text from Kayak, our flight was already gone. I’ll never use Kayak again and will go direct to the airlines in the future.

Boarding took forever, the plane was cramped and cold, and the seatbelt song came on constantly throughout the red eye flight with a loud pre-recorded message playing each time

Cabin felt crammed Snacks are lame But crew was super efficient getting us out on time despite delay

Took off on time and successfully avoided weather that looked to be a problem along the way

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

Flight was delayed a bit, but that was expected (and updated), so really not bad at all for the price. Could’ve used one less email asking me to upgrade my seat; otherwise no significant complaints

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

Flight was 2hours late they had no crew or the pilot.

I paid for streaming wifi and the connection was poor.

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Everything you need to know for your flight to Pleasant Prairie

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