28 Affordable Ways to Play and Stay in Chicago This Winter

There are countless ways to experience the best of Chicago during the winter months. Fill your weekend with free attractions, theater and dining deals, and special winter packages at some of the city’s finest hotels.

Free Things To Do

Millennium Park

It’s your kind of town square, home of the sculpture officially called Cloud Gate—aka The Bean. In winter, the park’s most popular winter activity is the ice skating rink that operates for four months a year. Another popular winter happening is Caroling at Cloud Gate, billed as part concert, part sing-along during the holidays. No matter the season, swing by the Park Grill restaurant in the heart of the park for beautifully plated American cuisine.

Navy Pier

The new Centennial Wheel dominates the scenery at the state’s most popular draw, but there are plenty of other gems to discover here, too, including a gallery of stained glass, the Chicago Shakespeare Theater and Amazing Chicago’s Funhouse Maze. While admission to Navy Pier is free, note that fees are charged for individual experiences.

Museum Campus

You can easily fill a day—or two—hopping among the three world-class museums dotting this park along Lake Michigan: the Adler Planetarium, the Shedd Aquarium and the Field Museum of Natural History. Illinois residents receive free admission on select days (check individual websites for details).

Skating Ribbon at Maggie Daley Park

Think outside the rink. This winding quarter-mile track offers gentle curves and rises.

National Museum of Mexican Art

The 10,000-piece collection in the heart of the city’s Mexican community is a cultural treasure.

The Oriental Institute, University of Chicago 

Browse artifacts from the ancient Near East, including Egypt, Persia, Syria and Nubia. Exhibits range from towering statues of King Tut to tiny fragments of the Qur'an and a child's pull toy from 2350 BC. 

Lincoln Park Zoo

Walk on the wild side—from aardvark to zebra—in the shadows of the skyline. It’s one of the nation’s few free zoos.

Lincoln Park Conservatory

Towering palms, ancient ferns and exotic orchids thrive in a charming Victorian-Era glass house.

Garfield Park Conservatory

Experience a greenhouse effect at this world-class indoor paradise of plants. 

Clarke House Museum

The city’s oldest home, an 1836 Greek Revival, sits in a park and shows how a pre-Civil War middle-class family lived.

Money Museum at the Federal Reserve Bank of Chicago 

Stop in at this museum in Chicago’s financial district to take pictures with $1 million, learn how to detect fake bills and catch up on the history of U.S. currency. 

The Art Institute of Chicago

Hey, parents of budding artists: Admission is always free for kids 13 and younger. Architecture, medieval armor, photography, European sculptures and Impressionist art are just a few of the collections inside the eight-building complex in the heart of the city. 

Chicago Cultural Center 

The world’s largest Louis Comfort Tiffany dome, composed of 30,000 stained-glass pieces, crowns the neoclassical 1897 Chicago Cultural Center (free tours offered). Also, enjoy complimentary concerts, performances, films and art exhibits. 

 

Free Tours

InstaGreeter 

If you ever longed for a Chicagoan friend to play tour guide on your visit, the InstaGreeter tours might be perfect for you. Tours leave from the Chicago Cultural Center on the half hour, Friday to Sunday. 

Millennium Knickerbocker 

Every Friday at 4 p.m., hotel concierge Paul Funkhouser takes visitors back to the Roaring ’20s when this was the Davis Hotel and Al Capone’s brother, Ralph, operated a speakeasy and casino on the hotel’s 14th floor. The tour takes guests through a ballroom that had the only lighted dance floor in Chicago and up to the mezzanine level that was home to a 5,000-volume library before it became a USO during World War II. 

Harold Washington Library Center 

At 10-stories tall and more than 750,000 square feet, the Harold Washington Library Center takes up a full city block and even has its own train stop. So, it should come as no surprise that the monthly art tour lasts a full two hours. Retired art librarian Anji Holtzman leads small group tours through the $1 million collection of paintings, photographs, sculptures, murals, Civil War-Era furnishings and cannon.  

 

Chicago Restaurant Week

Want an amazing prix fixe meal for an unbeatable price? Visit one of 370-plus restaurants during Chicago’s popular restaurant week, January 26–February 8, 2018. Yes, it’s technically two weeks instead of one, but that just means more time to explore the city’s diverse dining options. Brunches and lunches start at $22, dinner starts at $33 per person.

 

Chicago Theatre Week

 From February 8–18, 2018, many of the city’s 250 theaters offer steep discounts on tickets (some go for less than $15) for their productions. It’s all to celebrate Chicago’s world-class theater scene. When it isn’t theater week, you can score half-price seats a day or two before showtime via hottix.org or in person at one of two downtown locations (72 E. Randolph St. and 108 N. State St.).

Hotel Deals

Fairmont Chicago Millennium Park

The Fairmont makes it easy to give back while getting a good night’s rest with the Trees of Hope package. Each night of your stay equals a $10 donation to SOS Children’s Villages Illinois, plus you get 10 percent off the daily rate. Through March 21, 2018.

Radisson Blu Aqua

Avoid the “Where do I park and how much is it going to cost?” hassle with the Radisson Blu Aqua’s You Drive, We Park package that includes valet parking for one car per night. Simply pull up to the front drive and you’re good to go. Through April 5, 2018.

Warwick Allerton Hotel

The Warwick and Macy’s Shopping Experience package offers the ultimate shop-and-stay experience with a 3-minute mini-makeover, a MyStylist personal shopping appointment and a 15 percent discount on Macy’s merchandise. Through January 31, 2018.

The Peninsula Chicago

With so much to pack into a Windy City getaway, staying two nights simply isn’t enough. Get your third night for free when you book the More Time…With Our Compliments package through March 31, 2018.

Hotel Felix

Beat the lines at the Field Museum’s massively popular Jurassic World: The Exhibition with the Jurassic World Package through January 7, 2018. The deal includes accommodations, hotel breakfast for two guests and two VIP tickets to the exhibit.

Waldorf Astoria Chicago

Score a deal on serenity with the Waldorf Winter package through February 28, 2018. This offer features 10 percent off spa treatments, 15 percent off restaurants on-site and complimentary parking. 

The Blackstone Hotel

It’s the perfect time of year to play indoors at the Museum of Science and Industry. Get two tickets to the interactive playground of exhibits, plus two craft cocktails at Timothy’s Hutch, the hotel’s new lobby lounge. The Museum of Science and Industry Package is offered through March 31, 2018.

Thompson Chicago

Get a jump-start on New Year’s resolutions with the Raise the Barre for 2018 package. The deal includes a weekend pass to one of four Barre Code women’s fitness studios in Chicago, plus free workout swag and an assortment of healthy snacks and drinks. 

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