Southeast Wisconsin Vacation Packages 2026 from $199

Southeast Wisconsin flight + hotel vacation packages

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

Bridgeview Inn Chicago Area

Save 100% on your flight

$199

per person

Apr 23 - Apr 27

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Hotel Riu Plaza Chicago

Downtown Chicago

$543

per person

May 3 - May 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

$415

per person

Apr 30 - May 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

The Emily Hotel

Downtown Chicago

$457

per person

May 3 - May 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

$367

per person

May 3 - May 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Top Southeast Wisconsin hotels deals

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$159 total

Mar 8 - Mar 9

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

Saint Kate - The Arts Hotel

139 E Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$150 total

Feb 22 - Feb 23

Total with taxes and fees

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

Free WiFi

The Knickerbocker on the Lake

1028 East Juneau Avenue Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$113 total

Feb 24 - Feb 25

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Spa

Free WiFi

#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms

Twin Lakes WI

Get rates

This vacation home features an indoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A garden, laundry facilities, and concierge services are also on offer.

Pool

Hot Tub

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$194 nightly

$216 total

Feb 25 - Feb 26

Total with taxes and fees

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 lazy river, mini golf, and kid-friendly dining.

Pool

Hot Tub

Potawatomi Hotel & Casino

1611 West Canal Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$164 total

Feb 24 - Feb 25

Total with taxes and fees

A casino, 7 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free valet parking. Free self parking, a 24-hour business center, and a coffee shop are also offered.

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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

American Family Field

4.5/5(769 reviews)

Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.

Harley-Davidson Museum

4.5/5(337 reviews)

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.

Milwaukee County Zoo

4.5/5(217 reviews)

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

Frequently asked questions

How much are vacation packages to Southeast Wisconsin?

Starting at just $199, flight and hotel packages are a fabulous way to make your travel budget stretch further. Southeast Wisconsin, here you come!

Where can I get the best vacation package deals for Southeast Wisconsin?

With around 400 airline partners and 1,000,000 properties around the world, it's hard to top Travelocity. Take advantage of our extensive range and score an incredible Southeast Wisconsin package deal. Isn't it great when vacation planning is that easy?

Why should I purchase my Southeast Wisconsin vacation package via Travelocity?

From our 24/7 customer support to our range of exhilarating destinations, we are committed to giving you the vacation of a lifetime. All you need to do is click and book — our Price Match Guarantee will make sure you score the best deal.

Can I save money on my Southeast Wisconsin car rental if I bundle it with hotels and flights?

You certainly can with our Southeast Wisconsin vacation packages. With one of these, there are lots of ways to make your travel budget go further. Combine any two or more car, flight, hotel and tour bookings and watch your savings start to grow. With a rental car, all the popular sights in and around Southeast Wisconsin are a fun road trip away.

Which airport is best for Southeast Wisconsin?

Book an airfare to General Mitchell Intl. Airport (MKE) or Dane County Regional Airport (MSN). They are the main options for those traveling in and out of Southeast Wisconsin.

What is there to do in Southeast Wisconsin?

A vibrant and lively destination, Southeast Wisconsin offers some wonderful tourist attractions. American Family Field and Mitchell Park Horticultural Conservatory are two of the favorites.