Looking for lesser-known things to do in Chicago? Whether you’re just new in town or have been a local for a long time, it’s easy to see what sells Chicago. The world-class museums, parks, and architectural marvels like the Willis Tower skyscraper. Or the Frank Lloyd Wright masterpiece, Robie House. Then there’s the Chicago deep-dish pizza and the jazz club scene unique to the city.

But maybe there are some things you don’t yet know about the Second City. To help you out, we’ve selected some hidden gems to discover off the beaten path.


The Pedway

Interior look at the Chicago Pedway rock climbing wall

The Pedway is a buried treasure. Even long-term locals and pedestrians that walk right above the Pedway have no idea it exists. It’s a series of underground tunnels and bridges linking 40 blocks in the central business district. The walkways are filled with stores, art, and even a swimming pool.
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One of the great places it connects to is the architectural wonder, the Cultural Centre. On arrival, you can marvel at the world’s largest Tiffany dome – the mosaics and stained glass are absolutely beautiful.


Music Box Theatre

If Hollywood blockbusters aren’t your thing, you’ll be right at home at the Music Box. It’s Chicago’s go-to venue for independent, foreign, cult, and classic films. The two-screen cinema also hosts director Q&A’s and weekly midnight screenings. Also, their lounge and garden area serve specialty cocktails and a range of local and craft beers – a great spot to discuss film or meet for a drink. Plus, the popcorn comes with real butter.


Garfield Park Conservatory

the fern room at Garfield Park Conservatory

Who wouldn’t want to visit a place known as “landscape art under glass”, aka Garfield Park Conservatory? A peaceful spot away from the city, it’s also one of the largest conservatories in the nation. It houses eight indoor display gardens. Aside from the lush flora, what’s really interesting are the and donation-based activities and events they offer. Like yoga surrounded by the conservatories landscapes. Or Sweet Saturdays, where you can discover new tropical treats and taste your way through the fruits and vines on-site.


Brown Elephant

If you love thrifting, Brown Elephant is a must. There is a huge selection of thrifty finds here ranging from LP’s, clothing, home decor and more. It offers great values for a great cause. Donated and purchased items are used to raise money for the Harold Brown Health Center, an LGBTQ organization based in Chicago. If you’re looking for homeware for your apartment, this is a great spot for bargain hunting. Sometimes it’s a hassle to find the right furnishing to match the space of your apartment, especially if you’re moving around a lot. An advantage of renting a furnished apartment, like those by Blueground, is that the spaces come fully-furnished. So you can move in right away to professionally designed spaces with high-quality furnishings. But you can still make the place your own with some thrifted knick-knacks.


Thorne Miniature rooms

Thorne Miniature rooms

See something out of the ordinary at the Thorne Miniature Rooms, located downtown by Millennium Park. Rediscover your child-like curiosity peering into a collection of 68 dollhouses. They detail miniature re-creations of English, French and American household interiors ranging from the 13th to the 19th century. These tiny windows into a larger world were conceived by Mrs. James Ward Thorne of Chicago. They were modeled between 1932 and 1940 by master craftsmen to her specifications. The miniature rooms are located in the overlooked basement area of the Art Institute of Chicago.


Game Room

For an old-world atmosphere, check out the Game Room. It’s a lesser-known spot hidden in the Chicago Athletic Club hotel building. A retro cocktail lounge with a range of games, chess tables, foosball and more. You can even play on a full-sized bocce court, glass in one hand, ball in the other. Plus snack on street food like fish tacos and fried chicken sandwiches. It’s a fun spot for a group activity and an afternoon with friends.


Montrose Point Bird Sanctuary

Montrose Point Bird Sanctuary

You don’t have to be hardcore bird enthusiast to experience the Montrose Point Bird Sanctuary. It often flies under the radar, despite being located within city reach with the feel of being more rural. Visitors concur that the stunning views of downtown Chicago and Lake Michigan are worth the visit alone. Then there are the calm walking paths through the area to stroll along. Or the pleasure of being up close and personal with over 300 species of birds in the wooded areas of the bird sanctuary. It’s a nature lovers dream. The best time of day to visit is the morning – ideal for early birds.


Original Rainbow

Ice cream, anyone? The Rainbow Cone is just the ticket, a rite of passage on any culinary tour of the city. The ice cream shop has been serving their original rainbow cone to those in the know since 1926. Still the same today, their star attraction ice cream cone contains five flavors poured by exact order. From bottom to top: Chocolate, Strawberry, Palmer House (New York Vanilla with cherries and walnuts), Pistachio and Orange Sherbet. That fact it’s tucked away in one of the South Side’s most architecturally arresting neighborhoods – the historic Beverly – just adds to the nostalgic experience.


Maxwell Street Market

woman shopping at an outdoor market in chicago

For something different to do on a Sunday, stop by Maxwell Street Market where no two Sundays are the same. On-site they have authentic Mexican and Latino street food and a sprawling flea market. It was started in 1847 by the area’s immigrant communities, which is still evident today in the diverse range of market vendors. If you love rummaging around to find something unexpected, you’ll find antiques to furniture and everything in between.


Smart Bar

The Smart Bar, located in lively Wrigleyville, is a time-tested mecca for underground dance music. The venue mixes musically diverse local talent with a range of internationally famous guests. Other than hearing the most cutting edge DJs from around the globe, it’s also a spot for seeing up-and-coming acts who evolve into household names. Like The Black Madonna, an artist who cut her teeth behind the Smart Bar’s decks. If you like electronic music, make sure not to miss this iconic club.

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