$99 Cheap flights to Kenosha County

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Top places to visit in Kenosha County

An aerial view of a coastal city with a marina filled with boats, a lighthouse, and a large body of water.
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Kenosha

Kenosha
A pond surrounded by grass and trees, with a wooden bridge in the background.
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Pleasant Prairie

Pleasant Prairie
A mountain lake with autumn foliage and rugged terrain.
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Twin Lakes

Twin Lakes

Cheap flights to Kenosha County from $99 One Way, $191 Round Trip

$191 return flights and $99 one-way flights to Kenosha County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 5 - Sat, Aug 8
BOS
Boston
MKE
Milwaukee
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Select United flight, departing Wed, Aug 5 from Boston to Milwaukee, returning Sat, Aug 8, priced at $191 found 5 days ago
Thu, Aug 20 - Sat, Aug 29
BOS
Boston
MKE
Milwaukee
$193 Roundtrip, found 4 days ago
$193
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Aug 20 from Boston to Milwaukee, returning Sat, Aug 29, priced at $193 found 4 days ago
Wed, Sep 2 - Wed, Sep 9
BOS
Boston
MKE
Milwaukee
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Boston to Milwaukee, returning Wed, Sep 9, priced at $197 found 3 days ago
Thu, Oct 8 - Mon, Oct 12
DCA
Washington
MKE
Milwaukee
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 8 from Washington to Milwaukee, returning Mon, Oct 12, priced at $197 found 3 days ago
Tue, Sep 22 - Tue, Sep 29
BOS
Boston
MKE
Milwaukee
$197 Roundtrip, found 7 hours ago
$197
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Tue, Sep 22 from Boston to Milwaukee, returning Tue, Sep 29, priced at $197 found 7 hours ago
Wed, Sep 16 - Thu, Sep 17
DCA
Washington
MKE
Milwaukee
$199 Roundtrip, found 4 days ago
$199
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 16 from Washington to Milwaukee, returning Thu, Sep 17, priced at $199 found 4 days ago
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Find The Perfect Hotel For After Your Flight

Score Epic Kenosha County Accommodation Deals

Best Western Executive Inn Kenosha/Pleasant Prairie

Best Western Executive Inn Kenosha/Pleasant Prairie

2.5 out of 5
7220 122nd Ave Kenosha WI
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $86 total per night from Aug 2 to Aug 3
$86 total
Aug 2 - Aug 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.8/10 Excellent! (1,018 reviews)
"I would definitely recommend. The property could use an update but it was clean, convenient (good location and close to restaurants and shopping), and the staff was friendly and attentive to needs. I would book again."

Reviewed on Jul 12, 2026

Opens in a new windowBest Western Executive Inn Kenosha/Pleasant Prairie
Days Inn by Wyndham Pleasant Prairie Kenosha

Days Inn by Wyndham Pleasant Prairie Kenosha

2.5 out of 5
7540 118th Ave Pleasant Prairie WI
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $81 total per night from Jul 21 to Jul 22
$81 total
Jul 21 - Jul 22
Total with taxes and fees
Book a stay at this family-friendly hotel in Pleasant Prairie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Opens in a new windowDays Inn by Wyndham Pleasant Prairie Kenosha
The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
5706 8th Ave Kenosha WI
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $124 total per night from Jul 19 to Jul 20
$124 total
Jul 19 - Jul 20
Total with taxes and fees
Book a stay at this business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,013 reviews)
"Overall, we had a good stay at The Stella Hotel for three nights. The hotel itself is beautiful, the room was clean, and the location is excellent. It’s within walking distance of several restaurants, and being directly across from an ice cream shop made it easy to grab dessert every evening. Parking ..."

Reviewed on Jul 13, 2026

Opens in a new windowThe Stella Hotel & Ballroom
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Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $248 total per night from Jul 20 to Jul 21
$248 total
Jul 20 - Jul 21
Total with taxes and fees
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (1,378 reviews)
"We stayed at Harbor Shores for two nights and it was great! It’s literally across the street from the lake and a minutes walk from anywhere in downtown. The staff provided a list of suggestions on where to go for the best dining and each place we tried was excellent. The room was nice and had everything ..."

Reviewed on Jul 13, 2026

Opens in a new windowHarbor Shores on Lake Geneva
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Kenosha County

Get the absolute lowest prices on flights to Kenosha County by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Kenosha County Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Kenosha County flights.

Avoid Check-In Hassles When Traveling On Flights to Kenosha County

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Kenosha County flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Kenosha County flight using Orbitz.

Frequently asked questions

Which airlines fly to Kenosha County?
With 12 airlines waiting to whisk you away to Kenosha County, finding the ideal flight will be a piece of cake. Reserve your ticket with one of these major carriers that operate services to O'Hare Intl. Airport (ORD):

  • United Airlines - 612 flights to Kenosha County per month
  • American Airlines - 339 flights to Kenosha County per month
  • Air Canada - 190 flights to Kenosha County per month

How much is a flight to Kenosha County?
Return fares fell as low as $191 this past week to Kenosha County, and went as high as $199. Some lucky travelers journeying out of Washington (DCA) managed to bag one-way fares from just $99.
How to book the cheapest flight to Kenosha County?
With Orbitz, you'll uncover some of the most impressive flight deals around from a wide selection of airlines. But if you'd like to boost your chances of nabbing cheap flights to Kenosha County, here are a few pointers to consider:

  • Taking off from or arriving at other airports can be more cost-effective. Enter your preferred departure and arrival points. Next, select the 'Nearby airports' function below the form fields to see your options.
  • If your travel plans aren't set in stone, click on the 'Show flexible dates' option to see the flight deals for a range of departure dates. You may find an amazing fare.
  • You can also select the 'Show options' function to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you'd prefer to fly.
  • The early bird catches the most rewarding savings, so purchase your seats once you've settled on your travel dates. The most affordable fares get snapped up fast and prices climb as the departure date nears.
  • Bundle your flights, hotels and car rental into a package deal and score great discounts. Save your hard-earned money for things you're really excited about, like exploring Kenosha County.
  • Don't fly during the busy season if possible. By avoiding school vacations and summer, you can save loads on your airfare.

What is the best time to book a flight to Kenosha County?
On average, the cheapest month to book a seat is January. This is closely followed by February and August. When searching for a cheap flight to Kenosha County, it's always good to be ready to book. Cheap deals appear quickly and don't wait around!
What day of the week is the cheapest to book a flight to Kenosha County?
Land a fantastic flight deal by making a booking on a Tuesday, Wednesday or Saturday. These are typically the best days to land cheap tickets to Kenosha County.
What is the cheapest day of the week to fly to Kenosha County?
You can nab cheap flights to Kenosha County by taking off on a Monday, according to Orbitz data from 2020. Tuesday is the next cheapest day, while Saturday has the most costly airfares. Whether you prefer to save cash or fly on any day that's convenient, you'll always get a fabulous deal with Orbitz.
What is the cheapest month to fly to Kenosha County?
To pick up cheap flights to Kenosha County, you should pack your suitcase and take off in August. Orbitz data shows that this is generally a great month to save serious money on your ticket. If you're hoping to jet to Kenosha County during June, keep in mind that this is the most expensive time of year to take a trip.
Which airlines allow free cancellation?
Life changes, and we think your flight should be able to do the same. That's why Orbitz makes it a snap to search for flights with free cancellation and no change fees. Just enter your departure and arrival points and then select "Filter by flexible change policies." You can't beat that for peace of mind!
What do I need for the flight to Kenosha County?
There's nothing like jetting to a new place, but it pays to be prepared. This list of practical tips will help get your journey off to a great start:

  • Before you step on to the plane, you'll need to show some sort of government-issued ID, like a passport. You'll also need your ticket. If you're traveling with children, check with your airline about which documents they may need.
  • Make time fly by even quicker on your short hop by packing the right things. Think yummy snacks, bottled water and entertainment. If you want your journey to Kenosha County to pass nice and peacefully, put some headphones into your carry-on bag as well.
  • Whatever the weather outside, plane cabins can get chilly. Bring a light jacket on board to stop the goose bumps.

How do I get cheap first-class/business deals to Kenosha County?
There are ways of booking business or first-class fares to Kenosha County that won't burn a hole through your budget. Bag a seat in the pointy end of the plane for less with these useful tips:

  • Be flexible with your travel dates and hold out for deals on business or first-class airfares.
  • Look for a low-cost carrier that offers seats in business class. They often come with extra legroom and a glass of Champagne — and a more attractive price.
  • Make the most of your airline's loyalty program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction.

What is the best time to go to Kenosha County?
Tourists come from all over the place to visit Kenosha County in April, May and August. So if you love the idea of exploring this exciting destination in the busy season, this is the best time to go. As with many places in the Northern Hemisphere, summer commences June 20 in Kenosha County, with average daily temperatures hovering between 65 ºF and 75 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.