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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.
Holiday Inn Express Milwaukee Downtown by IHG

Holiday Inn Express Milwaukee Downtown by IHG

2.5 out of 5
Price was $662, price is now $591 per person
$591
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a fitness center. 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.
Clean

Reviewed on Oct 9, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Price was $1,202, price is now $988 per person
$988
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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.

Wildwood Lodge

Wildwood Lodge

2.5 out of 5
Price was $990, price is now $852 per person
$852
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Pewaukee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions K1 Speed and Center Court Sports Complex are located nearby.

County Clare Irish Hotel & Pub

County Clare Irish Hotel & Pub

2.5 out of 5
Price was $856, price is now $743 per person
$743
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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 American Family Field and Fiserv Forum are located nearby.

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Price was $980, price is now $861 per person
$861
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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.
I had to check in early due to an upcoming event and the front desk staff person couldn’t have been more helpful. The room was perfect and fit the vibe of the hotel. The staff at the bar outside were attentive. I’ll definitely be back!

Reviewed on Oct 11, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was $1,033, price is now $909 per person
$909
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) 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 The Rave-Eagles Club are located nearby.
Remodeled rooms, Very nice

Reviewed on Oct 10, 2026

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
Price was $680, price is now $603 per person
$603
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions American Family Field and Fiserv Forum are located nearby.

Ramada by Wyndham Milwaukee

Ramada by Wyndham Milwaukee

3.5 out of 5
Price was $923, price is now $822 per person
$822
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Milwaukee (MKE)
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, a free area shuttle, and a free cruise terminal shuttle. Popular attractions American Family Field and The Rave-Eagles Club are located nearby.

Waukesha Vacation Packages 3-4 Night Stays

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
Downtown Milwaukee
Price was $856, price is now $743 per person
$743
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Milwaukee (MKE)
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $1,202, price is now $988 per person
$988
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Milwaukee (MKE)
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
Westown
Price was $1,239, price is now $1,069 per person
$1,069
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Milwaukee (MKE)
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $980, price is now $861 per person
$861
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Milwaukee (MKE)

Waukesha Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Milwaukee Airport by IHG

Candlewood Suites Milwaukee Airport by IHG

2.5 out of 5
Price was $892, price is now $714 per person
$714
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Milwaukee (MKE)
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $1,285, price is now $1,035 per person
$1,035
per person
Nov 29 - Dec 4
found 23 hours ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $1,589, price is now $1,331 per person
$1,331
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Milwaukee (MKE)
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
Marquette
Price was $1,026, price is now $872 per person
$872
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Milwaukee (MKE)

Top Flight Deals

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

Frontier Airlines
Tue, Nov 24 - Wed, Nov 25
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$128 Roundtrip, found 7 hours ago
$128
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Nov 24 from Orlando Intl. to General Mitchell Intl., returning Wed, Nov 25, priced at $128 found 7 hours ago
Southwest Airlines
Mon, Nov 23 - Mon, Dec 7
DEN
Denver Intl.
MKE
General Mitchell Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Nov 23 from Denver Intl. to General Mitchell Intl., returning Mon, Dec 7, priced at $237 found 1 day ago
Sun Country Airlines
Wed, Nov 25 - Sun, Nov 29
MSP
Minneapolis - St. Paul Intl.
MKE
General Mitchell Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day 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 1 day ago
Bargain Flight
Wed, Nov 4 - Thu, Nov 26
DFW
Dallas-Fort Worth Intl.
MKE
General Mitchell Intl.
$258 Roundtrip, found 1 day ago
$258
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Nov 4 from Dallas-Fort Worth Intl. to General Mitchell Intl., returning Thu, Nov 26, priced at $258 found 1 day ago