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Weekend Getaways From Chicago


Canoe Bay

If you are looking for romantic weekend getaways from Chicago, check into Canoe Bay, a 280-acre estate with three private lakes in northwestern Wisconsin. There are just 19 ...

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West Baden Springs Hotel

Vacation Ideas from Chicago


Time to Get Away and Other Specials in Chicago from $219

The city is home to many wonderful wellness centers which can make you feel pampered and relaxed.

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mySpa in Chicago

Get a massage with your loved one in the beautiful couples suite or have a relaxing party with your girlfriends.

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3 Spa Weekend Trips from Chicago

Specials include accommodations, discounts on treatments and more.

Weekend Getaways from Chicago

Whether you are looking to relax on the beach, get pampered at a spa or go on a fun shopping trip, there is plenty to choose from within a few hours of Chicago.

Lake Geneva

A popular tourist destination year-round, Lake Geneva offers fun weekend activities which range from swimming to stargazing. The beautiful glacier lake features amazing sunsets, perfect for couples planning a romantic celebration.

Lake Geneva Cruise Line offers a unique perspective from the water and includes a historic tour of the area. You can also go on a romantic sunset cruise or a jazz dinner cruise. If you prefer to explore on your own, rent a kayak from Fontana Paddle Company.

Saugatuck, Michigan

BudgetTravel calls Saugatuck one of "The Coolest Small Towns in America", famous for its galleries, restaurants and a slower pace of life. Saugatuck Center for the Arts supports established and emerging artists with unique art exhibits and music events.

Accommodation options in Saugatuck include hotels, resorts, vacation rentals and charming inns. Check into the BaySide Inn which offers romantic rooms with views of the Saugatuck Harbor.


Milwaukee is an easy day trip from Chicago - take the Amtrak train which is more relaxing than driving and you won't have to worry about parking when you get there. The train ride takes an hour and a half. If you decide to spend the night, there are several reasonably priced accommodations in town.


About three hours from Chicago, Galena features historic mansions, wineries and several great spas. Top places to stay in Galena include Chestnut Mountain Resort, Goldmoor Inn and Eagle Ridge Resort & Spa.

Activities in the area include an alpine slide, Mississippi cruises, Segway tours, mini golf and biking. In the winter, there is skiing, snowboarding and kids’ programs.


Indianapolis is famous for its sports events, White River State Park, museums and an open-air music venue. Downtown has more than 25 hotels, offering accommodations options that range from affordable to upscale. Regardless of your taste in food, you will be able to find something that fits your palate at over 300 restaurants.

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