$95 Cheap flight deals from Cleveland (CLE) to Sheboygan (MKE)

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This Weekend's Flight Deals from Cleveland to Sheboygan

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, May 22 - Mon, May 25
CLE
Hopkins Intl.
MKE
General Mitchell Intl.
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 22 from Hopkins Intl. to General Mitchell Intl., returning Mon, May 25, priced at $277 found 2 days ago
Fri, May 22 - Mon, May 25
CAK
Akron-Canton
MKE
General Mitchell Intl.
$347 Roundtrip, found 5 days ago
$347
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, May 22 from Akron-Canton to General Mitchell Intl., returning Mon, May 25, priced at $347 found 5 days ago

Airfares from $95 One Way, $200 Round Trip from Cleveland to Sheboygan

Prices starting at $200 for return flights and $95 for one-way flights to Sheboygan were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Aug 10 - Tue, Aug 11
CLE
Cleveland
MKE
Milwaukee
$200 Roundtrip, found 2 days ago
$200
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Aug 10 from Cleveland to Milwaukee, returning Tue, Aug 11, priced at $200 found 2 days ago
Wed, Aug 26 - Mon, Aug 31
CLE
Cleveland
MKE
Milwaukee
$204 Roundtrip, found 2 hours ago
$204
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Cleveland to Milwaukee, returning Mon, Aug 31, priced at $204 found 2 hours ago
Wed, Jun 17 - Fri, Jun 26
CLE
Cleveland
MKE
Milwaukee
$210 Roundtrip, found 5 days ago
$210
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Jun 17 from Cleveland to Milwaukee, returning Fri, Jun 26, priced at $210 found 5 days ago
Tue, Aug 11 - Wed, Aug 12
CLE
Cleveland
MKE
Milwaukee
$280 Roundtrip, found 2 days ago
$280
Roundtrip
found 2 days ago
Select United flight, departing Tue, Aug 11 from Cleveland to Milwaukee, returning Wed, Aug 12, priced at $280 found 2 days ago
Tue, Aug 11 - Wed, Aug 12
CLE
Cleveland
MKE
Milwaukee
$285 Roundtrip, found 2 days ago
$285
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 11 from Cleveland to Milwaukee, returning Wed, Aug 12, priced at $285 found 2 days ago

Sheboygan economy flight packages

Price found within the past 48 hours. Click for updated prices.
Doubletree by Hilton Pleasant Prairie Kenosha
4.0-star property

Doubletree by Hilton Pleasant Prairie Kenosha

8.8/10 Excellent! (990 reviews)

Jul 1 - Jul 5

4 night stay

Cleveland (CLE) to Milwaukee (MKE)

United • Roundtrip • Coach
Price was $585, price is now $546 per person
$546
per person
just found
Room was very big and nice. The hot tub and pool were also very nice.

Reviewed on Feb 1, 2026

Plymouth Suites Hotel
2.0-star property

Plymouth Suites Hotel

7.4/10 Good! (28 reviews)

Jul 3 - Jul 6

3 night stay

Cleveland (CLE) to Milwaukee (MKE)

American Airlines • Non-stop roundtrip • Coach
Price was $823, price is now $762 per person
$762
per person
found 2 hours ago
AmericInn by Wyndham Plymouth
3.0-star property

AmericInn by Wyndham Plymouth

8.8/10 Excellent! (444 reviews)

Jul 3 - Jul 6

3 night stay

Cleveland (CLE) to Milwaukee (MKE)

American Airlines • Non-stop roundtrip • Coach
Price was $788, price is now $732 per person
$732
per person
found 2 hours ago
Stayed here two years ago and it was good.This time we stayed it was good. Perfect for sleeping, although I felt like the beds were full size, not the queen like specified. I didn't measure so I don't know. The one problem we had was the family above us was noisy. Maybe but children on first floor.

Reviewed on Oct 26, 2020

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More About Flying To Sheboygan from Cleveland

Route Information for Flights from Cleveland to Sheboygan

Origin Airport IATA Code
CLE
Destination Airport IATA Code
MKE
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Cleveland to Sheboygan

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Frequently asked questions

What is the shortest flight from Cleveland to Sheboygan?
The trip from Cleveland to Sheboygan can be as fast as 1 hour and 53 minutes. With a leisurely flight time like this, why not take off on an impromptu getaway?
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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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.