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Pleasant Prairie Vacation Packages

Build your package with 2 more options

Pleasant Prairie Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
County Clare Irish Hotel & Pub

County Clare Irish Hotel & Pub

2.5 out of 5
Price was $613, price is now $498 per person
$498
per person
Jan 27 - Jan 30
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Stay at this hotel in Milwaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Price was $766, price is now $566 per person
$566
per person
Jan 27 - Jan 30
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
Beautiful hotel in the perfect location. We had a lovely stay and are looking forward to future visits

Reviewed on Nov 9, 2026

Kimpton Journeyman Hotel by IHG

Kimpton Journeyman Hotel by IHG

4.5 out of 5
Price was $684, price is now $539 per person
$539
per person
Jan 27 - Jan 30
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Harley-Davidson Museum and Fiserv Forum are located nearby.
Clean rooms, beautiful rooftop bar

Reviewed on Nov 8, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Price was $798, price is now $642 per person
$642
per person
Jan 27 - Jan 30
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Harley-Davidson Museum and Fiserv Forum are located nearby.

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Price was $652, price is now $530 per person
$530
per person
Jan 27 - Jan 30
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Harley-Davidson Museum and Potawatomi Bingo Casino are located nearby.
Thank you again. Iron horse is the place to stay in MIL

Reviewed on Nov 8, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Price was $765, price is now $632 per person
$632
per person
Jan 27 - Jan 30
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Stay at this hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fiserv Forum and Harley-Davidson Museum are located nearby.
Super cool hotel- some of the art items brought back memories. Very friendly staff a go to at least once to experience it!

Reviewed on Nov 9, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was $770, price is now $642 per person
$642
per person
Dec 18 - Dec 21
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, free parking, and 7 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Potawatomi Bingo Casino and The Rave-Eagles Club are located nearby.
The rooms there dusty and the bed was uncomfortable..

Reviewed on Nov 9, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Price was $644, price is now $541 per person
$541
per person
Jan 27 - Jan 30
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, free parking, and a fireplace in the lobby. Our guests praise the clean rooms in our reviews. Popular attractions Harley-Davidson Museum and Potawatomi Bingo Casino are located nearby.

Pleasant Prairie Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Kimpton Journeyman Hotel by IHG

Kimpton Journeyman Hotel by IHG

4.5 out of 5
Downtown Milwaukee
Price was $684, price is now $539 per person
$539
per person
Jan 27 - Jan 30
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $836, price is now $606 per person
$606
per person
Dec 18 - Dec 21
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Milwaukee (MKE)
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $689, price is now $543 per person
$543
per person
Dec 18 - Dec 21
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Milwaukee (MKE)
Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was $798, price is now $642 per person
$642
per person
Jan 27 - Jan 30
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)

Pleasant Prairie Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
Avenues West
Price was $803, price is now $703 per person
$703
per person
Dec 20 - Dec 26
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $1,466, price is now $1,173 per person
$1,173
per person
Dec 20 - Dec 26
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $1,114, price is now $959 per person
$959
per person
Dec 20 - Dec 26
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was $1,188, price is now $1,034 per person
$1,034
per person
Dec 20 - Dec 26
found 8 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sun Country Airlines
Thu, Dec 17 - Fri, Jan 1
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$198 Roundtrip, found 11 hours ago
$198
Roundtrip
found 11 hours ago
Select Sun Country Airlines flight, departing Thu, Dec 17 from Orlando Intl. to General Mitchell Intl., returning Fri, Jan 1, priced at $198 found 11 hours ago
Sun Country Airlines
Wed, Dec 16 - Sun, Jan 3
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$207 Roundtrip, found 14 hours ago
$207
Roundtrip
found 14 hours ago
Select Sun Country Airlines flight, departing Wed, Dec 16 from Minneapolis - St. Paul Intl. to General Mitchell Intl., returning Sun, Jan 3, priced at $207 found 14 hours ago
Sun Country Airlines
Thu, Dec 17 - Thu, Dec 24
PHX
Sky Harbor Intl.
MKE
General Mitchell Intl.
$248 Roundtrip, found 2 hours ago
$248
Roundtrip
found 2 hours ago
Select Sun Country Airlines flight, departing Thu, Dec 17 from Sky Harbor Intl. to General Mitchell Intl., returning Thu, Dec 24, priced at $248 found 2 hours ago
Southwest Airlines
Wed, Jan 13 - Tue, Feb 9
DEN
Denver Intl.
MKE
General Mitchell Intl.
$259 Roundtrip, found 2 hours ago
$259
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Jan 13 from Denver Intl. to General Mitchell Intl., returning Tue, Feb 9, priced at $259 found 2 hours ago