Southeast Wisconsin Vacation Packages 2025/2026 from $250

Southeast Wisconsin flight + hotel vacation packages

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

Ameristar Casino Hotel East Chicago

Save 100% on your flight

$250

per person

Nov 13 - Nov 16

found 13 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This Art Deco hotel features a casino, a marina, and 5 restaurants. Enjoy the 24-hour gym and perks like free self parking. A bar/lounge, a 24-hour front desk, and a snack bar/deli are also provided.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$500

per person

Nov 7 - Nov 10

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.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$831

per person

Nov 25 - Dec 2

found 17 hours ago

Roundtrip flight included

Atlanta (ATL) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$542

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$485

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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

Top Southeast Wisconsin hotels deals

The Pfister Hotel

424 E Wisconsin Ave, Milwaukee, WI

$199 nightly

$234 total

Oct 9 - Oct 10

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

Hilton Milwaukee

509 W Wisconsin Ave, Milwaukee, WI

$99 nightly

$117 total

Nov 2 - Nov 3

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

Potawatomi Hotel & Casino

1611 West Canal Street, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$183 total

Oct 6 - Oct 7

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

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way, Lake Geneva, WI

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$215 total

Oct 7 - Oct 8

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

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$130 total

Nov 2 - Nov 3

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

The Iron Horse Hotel

500 W Florida Street, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$211 total

Oct 26 - Oct 27

Total with taxes and fees

This smoke-free hotel features 3 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A coffee shop, a terrace, and a library are also on offer.

Spa

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

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.

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 Art Museum

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 $250, 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.