Southeast Wisconsin Vacation Packages 2025/2026 from $242

Southeast Wisconsin flight + hotel vacation packages

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

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

$242

per person

Feb 4 - Feb 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

The Westin Michigan Avenue Chicago

Downtown Chicago

$473

per person

Dec 27 - Dec 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$251

per person

Feb 4 - Feb 8

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. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$254

per person

Feb 4 - Feb 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$263

per person

Jan 23 - Jan 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Top Southeast Wisconsin hotels deals

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$194 nightly

$216 total

Nov 19 - Nov 20

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

Hilton Milwaukee

509 W Wisconsin Ave Milwaukee WI

$68 nightly

$81 total

Dec 1 - Dec 2

Total with taxes and fees

This luxury 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

Free WiFi

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$153 total

Dec 14 - Dec 15

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

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$109 nightly

$129 total

Nov 19 - Nov 20

Total with taxes and fees

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

Free WiFi

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$130 total

Nov 26 - Nov 27

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 buffet breakfast each morning.

Pool

Hot Tub

Potawatomi Hotel & Casino

1611 West Canal Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$171 total

Dec 8 - Dec 9

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.

Parking included

Free WiFi

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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

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.

Milwaukee Art Museum

4.5/5(400 reviews)

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

Frequently asked questions

How much are vacation packages to Southeast Wisconsin?

Starting at just $242, 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.