Southeast Wisconsin Vacation Packages 2026 from $439

Southeast Wisconsin flight + hotel vacation packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$439

per person

Oct 22 - Oct 25

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.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$695

per person

Oct 22 - Oct 25

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.

The Pfister Hotel

Downtown Milwaukee

Save 100% on your flight

$987

per person

Oct 9 - Oct 12

found 4 hours ago

Roundtrip flight included

Dallas (DFW) to Milwaukee (MKE)

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. Relax with a drink at one of the 3 bars/lounges and enjoy the 24-hour gym.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$828

per person

Sep 13 - Sep 16

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.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$777

per person

Oct 15 - Oct 19

found 21 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.

Top Southeast Wisconsin hotels deals

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$223 total

Aug 23 - Aug 24

Total with taxes and fees

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$225 total

Aug 30 - Aug 31

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the indoor pool and perks like free self parking and free WiFi. There's a gym on site, and a 24-hour front desk and dry cleaning are also provided.

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$103 total

Aug 2 - Aug 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 gym and perks like free self parking.

AmericInn by Wyndham Brookfield

16865 W Bluemound Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$93 total

Aug 2 - Aug 3

Total with taxes and fees

This hotel features 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. Free self parking, a terrace, and a garden are also offered.

Potawatomi Hotel & Casino

1611 West Canal Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$177 total

Aug 2 - Aug 3

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.

The Cove Of Lake Geneva

111 Center St Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$279 nightly

$314 total

Aug 10 - Aug 11

Total with taxes and fees

2 hot tubs, an indoor pool, and a gym are all featured at this hotel. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. There's a restaurant and a bar/lounge for dining and drinks, and also a seasonal outdoor pool on site.

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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.

Stay near popular Southeast Wisconsin attractions

A baseball game in a stadium with a person holding a hot dog and a drink.

American Family Field

9.0/10 (2,832 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.

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Frequently asked questions

How much are vacation packages to Southeast Wisconsin?

Starting at just $439, 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.