Deals on vacations and trips to Southeast Wisconsin

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Southeast Wisconsin flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 23
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a terrace are also provided.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 6 - Jun 10
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 and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 1 - Jun 5
Roundtrip flight included
Newark (EWR) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 3 - Jun 7
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 23
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
A nightclub, a 24-hour gym, and a restaurant 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. You'll appreciate the a rooftop terrace, bar/lounge, and limo/town car service.

Top Southeast Wisconsin hotel deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave, Milwaukee, WI
Free Cancellation
Reserve now, pay when you stay
The price is $158 per night
$158
per night
May 19 - May 20
A full-service spa, 2 restaurants, and an indoor pool are all featured at this historic 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.
Pet friendly
Breakfast available
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave, Milwaukee, WI
Free Cancellation
Reserve now, pay when you stay
The price is $132 per night
$132
per night
May 5 - May 6
This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.
Pet friendly
Breakfast available
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Free Cancellation
Reserve now, pay when you stay
The price is $129 per night
$129
per night
May 5 - May 6
This smoke-free aparthotel features a golf course, free water park access, and a full-service spa. Take advantage of ski lessons, ski rentals and ski storage on site, and enjoy downhill skiing. Bring the family and enjoy the mini golf, children's pool, and kid-friendly dining.
Hot Tub
Fireplace
Hilton Milwaukee City Center

Hilton Milwaukee City Center

4 out of 5
509 W Wisconsin Ave, Milwaukee, WI
Free Cancellation
Reserve now, pay when you stay
The price is $119 per night
$119
per night
May 5 - May 6
This historic hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a garden are also offered.
Pet friendly
Breakfast available
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
333 W Kilbourn Ave, Milwaukee, WI
Free Cancellation
The price is $107 per night
$107
per night
May 5 - May 6
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.
Pet friendly
Breakfast available
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street, Milwaukee, WI
Free Cancellation
Reserve now, pay when you stay
The price is $135 per night
$135
per night
May 5 - May 6
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 buffet breakfast each morning.
Hot Tub
Pet friendly
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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.

Popular places to visit

Image for Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for Harley-Davidson Museum

Harley-Davidson Museum

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

Harley-Davidson Museum
Image for Milwaukee County Zoo

Milwaukee County Zoo

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo

Frequently asked questions

How much are vacation packages to Southeast Wisconsin?
Travelocity offers flight and hotel packages from an incredible $509. With such amazing bargains, you’ll be saying hello to Southeast Wisconsin in a flash.
Where can I get the best vacation package deals for Southeast Wisconsin?
No matter how you travel, Travelocity can help you snap up a great Southeast Wisconsin package deal. All you have to do is select a combination from our 400 airlines and 1,000,000 properties across the globe.
Why should I purchase my Southeast Wisconsin vacation package via Travelocity?
You’ll not only enjoy big savings, but you can also access our round-the-clock support, excellent service and a Price Match Guarantee. Explore every nook-and-cranny across the world, uncover hidden gems and forge unforgettable memories — we’ll take care of the little details.
Can I save on my Southeast Wisconsin car rental if I book it with a hotel or flight?
You can with our Southeast Wisconsin vacation packages. With one of these, there are lots of ways to make your travel budget go further. Bundle any two or more car, flight, hotel and tour bookings and watch the savings start to pile up. With your own ride, all the popular sights around Southeast Wisconsin are within your reach.
What is the best time of year to go to Southeast Wisconsin?
If you want to avoid costly airfares, huge crowds and overbooked hotels, organize your getaway outside of May, June and July. The quietest time to be in Southeast Wisconsin is November, December and January. You’ll find hotel rates are the highest in and the lowest in .
Which airport is best for Southeast Wisconsin?
General Mitchell Intl. Airport (MKE) and Dane County Regional Airport (MSN) are the two top airports for touching down in Southeast Wisconsin.