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Waukesha Vacation Packages

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Waukesha Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Save 100% on your flight
Price was $663, price is now $435 per person
$435
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 American Family Field and Fiserv Forum are located nearby.

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Price was $966, price is now $693 per person
$693
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 American Family Field and Riverside Theater are located nearby.
Love the themed rooms and hotel. Really comfortable rooms (with Victrola record players and record albums!!!). Onsite art museum. Excellent complimentary champagne upon checking in!!! Only disappointment is that the Studio Restaurant has ridiculous open/close hours. Plan accordingly! With that exception, definitely a new and fun place to return to. Btw, Pabst Theater is located within the building. 5 min walk from the lobby!! Super convenient!!

Reviewed on Aug 22, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Price was $641, price is now $481 per person
$481
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 American Family Field and Harley-Davidson Museum are located nearby.
We loved the Iron Horse Hotel! It was very clean, beautiful and perfect in every way. We liked that we could walk to the HD museum and that we could park our motorcycles for free. We loved the restaurant.

Reviewed on Aug 22, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Price was $540, price is now $444 per person
$444
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 American Family Field and Henry W. Maier Festival Park are located nearby.
Great Location. Nice restaurant in building.

Reviewed on Aug 20, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was $522, price is now $439 per person
$439
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 American Family Field and Harley-Davidson Museum are located nearby.

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Price was $697, price is now $588 per person
$588
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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 American Family Field and Riverside Theater are located nearby.
Every person we were with, had a problem with access codes. That became really annoying.

Reviewed on Aug 22, 2026

The Westin Milwaukee

The Westin Milwaukee

4 out of 5
Price was $626, price is now $529 per person
$529
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Milwaukee. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions American Family Field and Henry W. Maier Festival Park are located nearby.

Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
Price was $993, price is now $841 per person
$841
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Milwaukee (MKE)
Book a stay at this beach resort in Delavan. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Lake Lawn Resort Marina and Delavan Lake are located nearby.

Waukesha Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $663, price is now $435 per person
$435
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Milwaukee (MKE)
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $966, price is now $693 per person
$693
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $641, price is now $481 per person
$481
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Milwaukee (MKE)
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $540, price is now $444 per person
$444
per person
Nov 9 - Nov 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Milwaukee (MKE)

Waukesha Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $1,408, price is now $1,074 per person
$1,074
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $1,948, price is now $1,423 per person
$1,423
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Milwaukee (MKE)
Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Save 100% on your flight
Price was $1,406, price is now $1,090 per person
$1,090
per person
Oct 14 - Oct 21
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $1,622, price is now $1,294 per person
$1,294
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Milwaukee (MKE)

Top Flight Deals

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

Frontier Airlines
Thu, Oct 8 - Tue, Oct 20
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$151 Roundtrip, found 7 hours ago
$151
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Oct 8 from Orlando Intl. to General Mitchell Intl., returning Tue, Oct 20, priced at $151 found 7 hours ago
Delta
Wed, Sep 16 - Thu, Oct 1
DEN
Denver Intl.
MKE
General Mitchell Intl.
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 16 from Denver Intl. to General Mitchell Intl., returning Thu, Oct 1, priced at $211 found 1 day ago
Bargain Flight
Tue, Oct 27 - Wed, Oct 28
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$240 Roundtrip, found 6 hours ago
$240
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Tue, Oct 27 from Dallas-Fort Worth Intl. to General Mitchell Intl., returning Wed, Oct 28, priced at $240 found 6 hours ago
Sun Country Airlines
Wed, Nov 25 - Sun, Nov 29
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$247 Roundtrip, found 15 hours ago
$247
Roundtrip
found 15 hours ago
Select Sun Country Airlines flight, departing Wed, Nov 25 from Minneapolis - St. Paul Intl. to General Mitchell Intl., returning Sun, Nov 29, priced at $247 found 15 hours ago