Southeast Wisconsin Vacation Packages 2026 from $187

Southeast Wisconsin flight + hotel vacation packages

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

Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Save 100% on your flight

$187

per person

Feb 18 - Feb 21

just found

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A gym is featured at this hotel, along with self parking. WiFi in public areas is free. Traveling on business? Take advantage of the 3 conference rooms, 24-hour business center, and express check-out.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$355

per person

Feb 18 - Feb 22

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.

DoubleTree by Hilton Milwaukee - Brookfield

Save 100% on your flight

$306

per person

Feb 2 - Feb 8

found 7 hours ago

Roundtrip flight included

Atlanta (ATL) to Milwaukee (MKE)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$321

per person

Feb 18 - Feb 22

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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$347

per person

Feb 20 - Feb 22

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.

Top Southeast Wisconsin hotels deals

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$199 total

Jan 3 - Jan 4, 2026

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

Saint Kate - The Arts Hotel

139 E Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$151 total

Dec 28 - Dec 29

Total with taxes and fees

This smoke-free hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, a coffee shop, and express check-out are also offered.

Pet friendly

Free WiFi

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$194 nightly

$216 total

Jan 4 - Jan 5, 2026

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

Hilton Milwaukee

509 W Wisconsin Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$105 total

Dec 21 - Dec 22

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

The Iron Horse Hotel

500 W Florida Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$142 total

Dec 28 - Dec 29

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

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$118 total

Jan 1 - Jan 2, 2026

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

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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

4.5/5(337 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.

Milwaukee County Zoo

4.5/5(217 reviews)

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee Art Museum

4.5/5(400 reviews)

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 $187, 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.