While Chicago has plenty of icons that draw travelers from near and far, true Chicagoans know exactly where to find unique adventures that will help you get to know the real Windy City. Maybe you are looking for a rental house in Chicago to test the waters, or you want to buy a home near the heart of the city, or maybe your goal is to find an apartment overlooking Lake Michigan. Regardless of what you are looking for, these 16 hidden gems in Chicago are bound to make you feel home.
1. Enjoy an iconic Chicago-dog at Jeff’s Red Hots
“When in Chicago, it is non-negotiable to eat a Chicago-Style Hot Dog.” Jeff’s Red Hots has been around since 1977, serving Chicago and its visitors one of the best hot dogs in the city. Whether you’re moving into the Portage Park neighborhood or just passing through town, grabbing a Chicago-Style dog from this local, family-owned business is an absolute must.
2. Raise a glass at Pops for Champagne
“As a wine expert in the Chicago area, my number one must-visit is Pops for Champagne,” says Sommelier Jane Norrington of See Jane Drink Wine. Pops is the oldest wine bar in the U.S. dedicated to champagne, offering over 150 champagnes and hundreds of other varieties of wines from across the world. “The staff is next to none, and their food menu offers perfect pairings for your glass. My favorite? A glass of Domaine de Bichery Blanc de Blanc paired with French fries and Dijonnaise.”
3. Meet new people and take in Lake Michigan by bike
“Bike the Drive turns Lake Shore Drive into a cyclists’ paradise,” says Mariya, owner and photographer at Mariya S Photography. She highly recommends the annual event that takes place at Butler Field in The Loop neighborhood. Thousands of people bike to and from a 15-mile stretch of Lake Shore drive that closes to traffic for cyclists of all ages. “It’s such a thrilling event – you’re surrounded by the coolest people biking along a gorgeous skyline and watching the sunrise over Lake Michigan,” says Mariya.
4. Get into the fall spirit with Jack’s Pumpkin Pop Up
“If you’re looking for a fun fall outing, check out Jack’s Pumpkin Pop Up on Goose Island,” shares WeLovePopUps, your go-to resource for the best seasonal pop ups in Chicago. They have everything from a corn maze to cute photo spots, carnival games, and tasty fall drinks. “The whole place just screams cozy autumn vibes, and it is a perfect way to soak in the season with friends.” 
5. Make the most of an evening with a food tour
Lauren, owner of Stunning & Brilliant Events, a multi-city wedding planning team, recommends getting to know the flavors of Chicago with a food tour fit for any evening out on the town. “I suggest going for the king crab roll at Maple & Ash located in the Gold Coast,” says Lauren. “Then, pop over to The Bellevue across the street to sip and sit on the patio with their Greek salad. End the night at Adalina for a night cap – and don’t pass up their chicken parmesan pizza if it’s a Sunday.”
6. Discover Wonderverse, an immersive entertainment venue
There are countless things to do indoors and outdoors in Chicago, but Wonderverse is like entering a whole new world. Here is a little bit about them in their own words: “If you’re getting to know the city, make sure to add Wonderverse to your bucket list. Whether you’re looking for fun entertainment or virtuality experiences, Wonderverse has something for everyone. Enjoy NFL game days with platters and drink specials, test your knowledge with weekly trivia, or immerse yourself in themed events like our Halloween-inspired Hotel Transylvania Character Brunch. Wonderverse is the ultimate destination for family fun, food, and entertainment.”
7. Take a breath of fresh air at a nearby lake
“Escape the city for a day out on beautiful Lake Geneva with us at Lake Geneva Cruise Lines.” Take a day-trip to find the perfect cruise to fit the vibe you’re looking for. Offering numerous sightseeing and meal cruises, there is a one-of-a-kind boat tour for everyone on board. “Our narrated boat tours cruising through October are the best way to see the fall foliage around the lake and make for a fun fall adventure.”
8. Find amazing views and variety at the Museum Campus
Nate, portrait and lifestyle photographer at Nathaniel Smith Photographs, recommends exploring the numerous parks and museums in this unique area of the city. “The view of the city at night from the Museum Campus is unmatched. The museums are all top notch, it’s a perfect place to bike, and there are concerts at night in the summer at Northerly Island.”
9. Toast to a great evening with cocktails fit for a king
Get a mystical perspective at King of Cups Cocktail Lounge with a wonderful cocktail program sure to please any pallet. Located in the Lincoln Park neighborhood, dive into your future with one of their nightly tarot readings paired with a royal cocktail, or stop by for one of their amazing happy hours.
10. Get to know the city equipped with coffee and books
If you’ve just moved to Chicago and are a coffee enthusiast, Metric Coffee is the place to be. Located in the Industrial Corridor of the West Town neighborhood, they offer free cuppings and coffee tastings every Friday morning. Metric also suggests checking out MYOPIC Books in nearby Wicker Park. “This amazing bookstore is a local hidden gem for new and used books, and even hosts a variety of author events.”
11. Bring a taste of Michigan to your Chicago experience
Lola’s Coney Island in Humboldt Park is a prime example of the cuisine that makes Chicago one of the top places in the country to go for food. Grab a true authentic Coney-dog straight from Detroit, a classic Chicago-dog, or try one of Lola’s specially made hybrid versions.
12. The Windy City is only the beginning
On the local side, Andrew and Catie of Lesser Known Adventures recommend Ricobene’s for their famous steak sandwiches, but they love Chicago most for its close proximity to so much more. “Within an hour’s drive, you could be riding a roller coaster at Six Flags Great America or, if you’re a car enthusiast, checking out the largest collection of vintage and Hollywood movie cars at the Volo Auto Museum. And, if you’re in the mood for an epic road trip, Chicago is the starting point of the historic Route 66 – one of the best road trips in the world.”
13. Discover Christmas in Chicago
“Braving the cold is a Herculean task, but there is always something fun to make it worth it,” shares Joshua, manager of Overflow Coffee in the heart of the city. The Christkindlmarket, a German-style Christmas market for winter holiday fun. “They have great food, music, gifts, knickknacks, ice skating, spiced wine or hot chocolate served in collectible mugs, and tons of Christmas spirit. It is something you’ll want to make into a tradition for sure.”
14. Classic Italian comfort is just around the corner
Buona Terra Ristorante has been a beloved staple in the Irving Park community for the past 23 years. Best known for its authentic Italian cuisine and fresh, locally sourced menu, Buona Terra is perfect for a cozy dinner or a special occasion. It has become a favorite among Chicago residents as a delightful escape right in the neighborhood.
15. Attend one of the many neighborhood summer festivals
“Chicago is a city of neighborhoods,” shares travel blogger Travel With Meena, “each with a distinct character that comes through during these summer celebrations of local art, music, and food. Contribute to an interactive art piece or catch a canine fashion show at the Logan Square Arts Festival. Watch fire dancers, listen to local bands and sip on local brews at Wicker Fest, or dive into the city’s Scandinavian heritage at Andersonville Midsommarfest. This is the real Chicago.”
16. Marvel at the annual Chicago Air and Water Show
At the end of the summer, the Chicago Air and Water Show roars across the shore, bringing the largest free show of its kind in the U.S. to Lake Michigan. Susan, owner of local wedding planning company Big City Bride, says “It’s a perfect beach day to enjoy the lake when it’s at its warmest of the season. You can feel the electricity in the air when the Blue Angels rip through the sky.”
Hidden gems in Chicago: final thoughts
Whether you like to keep close to the heart of the city or embrace your adventurous side, living in Chicago will always have something exciting to offer. These hidden gems in and around the Windy City are sure to make Chicago feel more like home – regardless of how long you stay.
