Waukesha County Vacation Packages 2026 from $488

Search vacation packages deals in Waukesha County's top destinations

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Oconomowoc

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Waukesha County flight + hotel vacation packages

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

JW Marriott Chicago

Downtown Chicago

Save 100% on your flight

$488

per person

May 16 - May 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$717

per person

May 23 - May 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Eurostars Magnificent Mile

Downtown Chicago

Save 100% on your flight

$522

per person

May 16 - May 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Thompson Chicago, by Hyatt

Downtown Chicago

Save 100% on your flight

$913

per person

Jun 18 - Jun 21

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features 2 bars/lounges and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$626

per person

May 23 - May 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

Top Waukesha County hotels deals

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$110 total

Apr 20 - Apr 21

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like free self parking.

Pool

Free airport shuttle

Embassy Suites by Hilton Milwaukee Brookfield

1200 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$141 total

Apr 19 - Apr 20

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Country Inn & Suites by Radisson, Milwaukee West (Brookfield), WI

1250 S Moorland Rd Brookfield WI

Free Cancellation

$101 nightly

$117 total

Apr 19 - Apr 20

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

The Ingleside Hotel

2810 Golf Road Pewaukee WI

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$134 total

Apr 12 - Apr 13

Total with taxes and fees

A water park and an indoor pool are featured at this traditional hotel. Traveling on business? Take advantage of the 20 conference rooms, free WiFi in public areas, and express check-out. Enjoy the gym and perks like free self parking.

Pool

Pet friendly

Wildwood Lodge

N14 W24121 Tower Place Pewaukee WI

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$105 total

Apr 26 - Apr 27

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Pool

Hot Tub

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$223 total

May 3 - May 4

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the 24-hour gym and visit the 3 bars/lounges and poolside bar for drinks.

Pool

Spa

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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.

Photos of local treasures

Browse Waukesha County vacation photos for more inspiration

Looking at the boat launch on Genesee Lake in Waukesha County, Wisconsin. Lazy cumulus clouds are reflected in the calm lake waters.

A meticulously maintained putting green with the flagstick and pin visible, surrounded by lush grass and autumn trees in Waukesha County.

Frequently asked questions

How much are vacation packages to Waukesha County?

$488 is all you need to spend for an exciting vacation in Waukesha County. Bundle your flights and hotel into a Travelocity package and watch the savings start to pile up. With such good prices, there's never been a better time to travel.

Where can I get the best vacation package deals for Waukesha County?

There are amazing Waukesha County package deals to be scored with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties in all corners of the globe? Keep that in mind when you're ready to cross another destination off your list.

Why should I purchase my Waukesha County vacation bundle with Travelocity?

Whether you're planning an epic vacation or a last-minute trip, we have lots of enticing destinations to choose from at a good price. And on top of that, we provide 24/7 support, superb service and a Price Match Guarantee. Save yourself money and time and reserve your dream vacation now.

Can I save money on my Waukesha County car rental if I combine it with a hotel or flight?

Sure can. And our Waukesha County vacation packages are the perfect way to do it. With just a few clicks you can save cash and time by combining your bookings. Pick up the keys to your rental car then chart your own course. Need to fill your itinerary? Add some activities or experiences to your package and make savings on those too.

Which airport is best for Waukesha County?

General Mitchell Intl. Airport (MKE) and Dane County Regional Airport (MSN) are your top options for jetting to Waukesha County.

What is there to do in Waukesha County?

Waukesha County has hidden surprises around every corner, but make sure you get to Little Muskego Lake and Oconomowoc Arts Center while you're here. These attractions are popular with visitors.