Southeast Wisconsin Vacation Packages 2025/2026 from $342

Southeast Wisconsin flight + hotel vacation packages

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

Holiday Inn Chicago O'Hare – Rosemont by IHG

O'Hare

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a grocery/convenience store are also offered.

Chicago Athletic Association, a Hyatt Hotel

Downtown Chicago

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This smoke-free hotel's 2 restaurants, 3 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a coffee shop are also provided.

The Emily Hotel

Downtown Chicago

per person

Oct 22 - Oct 27

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. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Staybridge Suites Chicago O'Hare - Rosemont by IHG

O'Hare

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the free buffet breakfast each morning.

Arlo Chicago

Downtown Chicago

Save 100% on your flight

per person

Oct 22 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking and dry cleaning are also offered on site.

Top Southeast Wisconsin hotels deals

Harbor Shores on Lake Geneva

300 Wrigley Dr, Lake Geneva, WI

Free Cancellation

Reserve now, pay when you stay

$165 nightly

$187 total

Sep 1 - Sep 2

Total includes 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

The Pfister Hotel

424 E Wisconsin Ave, Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$205 nightly

$242 total

Sep 14 - Sep 15

Total includes 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

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way, Lake Geneva, WI

Free Cancellation

Reserve now, pay when you stay

$213 nightly

$238 total

Sep 16 - Sep 17

Total includes 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

Sonesta Select Milwaukee Brookfield

16865 W Bluemound Rd, Brookfield, WI

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$100 total

Aug 25 - Aug 26

Total includes taxes and fees

This hotel features an indoor pool and a 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 snack bar/deli are also offered.

Pool

Pet friendly

Lodge Geneva National

W4240 WI-50, Lake Geneva, WI

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$166 total

Sep 7 - Sep 8

Total includes taxes and fees

This resort features a restaurant, an indoor pool, and a bar/lounge. You'll appreciate the gym, poolside bar, and concierge services.

Pool

Pet friendly

AmericInn by Wyndham Glendale/Milwaukee

5110 N Port Washington Rd, (772), Milwaukee, WI

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$82 total

Sep 8 - Sep 9

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and wedding services.

Breakfast included

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 $342, 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.