Southeast Wisconsin Vacation Packages 2026 from $673

Southeast Wisconsin flight + hotel vacation packages

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

Level Chicago – Old Town

Downtown Chicago

$673

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boise (BOI) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$966

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boise (BOI) 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.

Stay One Chicago

Downtown Chicago

Save 100% on your flight

$1,387

per person

Nov 24 - Nov 30

found 4 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This smoke-free hotel includes 3 restaurants, an indoor pool, and A 24-hour gym. Enjoy the seasonal outdoor pool and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and coffee shop.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$863

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boise (BOI) 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 Talbott, Autograph Collection

Downtown Chicago

$684

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Boise (BOI) 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. Dry cleaning, luggage storage, and wedding services are also on offer.

Top Southeast Wisconsin hotels deals

The Pfister Hotel

424 E Wisconsin Ave Milwaukee WI

$194 nightly

$229 total

Sep 27 - Sep 28

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

Pool

Spa

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$166 total

Sep 15 - Sep 16

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Relax with a drink at the bar/lounge and enjoy the sauna.

Pool

Parking included

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$110 total

Sep 29 - Sep 30

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

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$151 total

Sep 20 - Sep 21

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

$181 nightly

$202 total

Oct 12 - Oct 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

The Iron Horse Hotel

500 W Florida Street Milwaukee WI

$181 nightly

$214 total

Oct 5 - Oct 6

Total with taxes and fees

This boutique hotel features 2 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

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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.

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Frequently asked questions

How much are vacation packages to Southeast Wisconsin?

Starting at just $673, 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.