Southeast Wisconsin Vacation Packages 2026 from $254

Southeast Wisconsin flight + hotel vacation packages

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

Le Méridien Essex Chicago

Downtown Chicago

Save 100% on your flight

$254

per person

Jan 19 - Jan 22

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

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

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Save 100% on your flight

$567

per person

Dec 19 - Dec 22

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

This smoke-free hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.

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

$685

per person

Dec 16 - Dec 23

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$293

per person

Jan 19 - Jan 22

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$349

per person

Jan 19 - Jan 22

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Top Southeast Wisconsin hotels deals

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$117 total

Nov 23 - Nov 24

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 a snack bar/deli are also offered.

Pet friendly

Free WiFi

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$100 total

Nov 8 - Nov 9

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.

Pool

Pet friendly

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$131 total

Nov 30 - Dec 1

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

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$197 total

Nov 10 - Nov 11

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

Motel 6 Milwaukee, WI - Glendale

5485 N Port Washington Rd Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$44 nightly

$51 total

Nov 8 - Nov 9

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Pet friendly

Parking included

Grand Geneva Resort & Spa

7036 Grand Geneva Wy Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$268 nightly

$299 total

Nov 24 - Nov 25

Total with taxes and fees

This smoke-free resort features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities.

Pool

Hot Tub

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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 sign for Miller Park, home of the Milwaukee Brewers, with a baseball and stars.

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.

See properties

Frequently asked questions

How much are vacation packages to Southeast Wisconsin?

Starting at just $254, 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.