Southeast Wisconsin Vacation Packages 2026 from $542

Southeast Wisconsin flight + hotel vacation packages

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

Fairmont Chicago at Millennium Park

Downtown Chicago

Save 100% on your flight

$542

per person

Jul 10 - Jul 13

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. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$631

per person

Jun 25 - Jun 28

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.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$692

per person

Jun 17 - Jun 21

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.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$753

per person

Jun 17 - Jun 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$987

per person

Jun 17 - Jun 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Top Southeast Wisconsin hotels deals

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$137 total

May 10 - May 11

Total with taxes and fees

This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Parking included

Potawatomi Hotel & Casino

1611 West Canal Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$165 nightly

$195 total

May 11 - May 12

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

The Iron Horse Hotel

500 W Florida Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$223 total

May 31 - Jun 1

Total with taxes and fees

This boutique hotel features 3 restaurants, a bar/lounge, and a 24-hour gym. Families will appreciate the arcade/game room and onsite laundry facilities. WiFi in public areas is free.

Spa

Pet friendly

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$186 nightly

$208 total

May 12 - May 13

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

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$119 total

May 10 - May 11

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, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like free self parking.

Pool

Free airport shuttle

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$131 total

May 25 - May 26

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

Don't see what you're looking for?

See all available properties in Southeast Wisconsin

View all properties

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(777 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(342 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.

Henry W. Maier Festival Park

4.5/5(132 reviews)

Enjoy an outing to Henry W. Maier Festival Park during your stay in Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Frequently asked questions

How much are vacation packages to Southeast Wisconsin?

Starting at just $542, 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.