Things to do for Trendsters in Chicago 

Filter attractions by: Category
Map view
Filter by
Sort By
Popularity - Overall
Grid ViewList View
1,635 Results
filtered byTrendstersX
Clear all
  • Recommended for You
  • 1

    Wicker Park

    24 reviews

    My hood! A cross between Brooklyn and Soho, trendy WP has so many fab restaurants and shops it's hard to keep track of all the new things opening. Standouts: Mana (vegetarian tapas, even though I'm as carnivore as they come), Bongo Room (white choc carmel pretzel die for), and Bangers and Lace (best grilled cheese / craft beers)

    Popular withTrendstersLocalFoodies
  • 2

    Violet Hour

    20 reviews

    An intimate, classy bar with potent cocktails is the perfect combination for an amazing night out. The cocktail menu is divided by liquor, and the drinks become stronger as you move through each category. The door is unmarked, and there's usually a wait to get in, so arrive early. I'll definitely return the next time I'm in Chicago.

    Popular withTrendstersLuxuryNightlife
  • 3

    Big Star

    23 reviews

    Come springtime, after nearly nine months of hibernation, Chicagoans practically sprint to this trendy taqueria in Wicker Park. With $30 pitchers of margaritas and an epic patio outfitted with sleek metal tables and sunshine yellow chairs, Big Star is where you come to while away a weekend afternoon with friends. Don’t be surprised if you see the same diners at ...

    Popular withFoodiesTrendstersNightlife
  • 4

    Second City

    45 reviews

    So happy a friend recommended checking Second City out! Great improv and good fun. Make sure to get tickets early as they sell out pretty quickly.

    Popular withLocalNightlifeTrendsters
  • 5

    Signature Lounge

    9 reviews

    If you want to see Chicago skyline views from above, without the 2-hour wait from the Willis Tower, then this is your place. Take the elevator to the 96th floor for a bar seat, a cocktail and sweeping views of the Windy City. For a proper dinner, make reservations ahead at the Signature Room. Both have spectacular views and reasonable ...

    Popular withTrendstersLuxuryNightlife
  • 6


    8 reviews

    My favorite bar in Chicago, hands down. The Aviary is essentially a four star restaurant, but without the actual kitchen component. But Aviary doesn't feel stuffy so much as it feels sharp, smart and inspired. Buy tickets for your cocktail tasting program in advance to secure a spot at the bar, but don't stress if you forget. They generally reserve ...

    Popular withTrendstersFoodiesLGBT
  • 7

    The Magnificent Mile

    86 reviews

    The Magnificent Mile a.k.a. North Michigan Ave is the "Fifth Ave" of Chicago. The area is a shopper's delight and it offers a broad range of retail stores from American Eagle Outfitters to Armani Exchange. There is something for everyone.

    Popular withLuxuryFamiliesTrendsters
  • 8


    9 reviews

    Whirlyball is lacrosse meets bumper cars! So much fun and so competitive! great for team building and celebratory parties! This game is a speciality sport in the Midwest and a must play when in the area!

    Popular withLocalAdventureTrendsters
  • 9

    Goose Island Brewpub

    11 reviews

    Not only can you get special brews here, but the food is outstanding! Definitely underrated.

    Popular withFoodiesTrendstersLocal
  • 10


    3 reviews

    This trendy speakeasy-style bar has quickly shot to the top of everybody's list of places to drink in Chicago. Choose a cocktail from the gin-centric menu, then relax by one of the two fireplaces. Stick around until midnight, when they pass out complementary chocolate chip cookies.

    Popular withTrendstersFoodiesNightlife
  • 11

    Museum of Contemporary Art

    23 reviews

    An attractive modern art museum with a nice sculpture garden. The collection here isn't quite on par with the great modern museums of the world but it is certainly worth a visit and is easy walking distance from Michigan avenue.

    Popular withDesignTrendstersLocal
  • 12


    7 reviews

    The new hit and surefire place to be this spring in Chicago has arrived. Definitely a must try if you are a visitor or resident. The food is tasty, assortment of cheeses and preserved meats and fresh made pastas are top flight, and the beer is good. If you choose to dine there, I would prefer one of the stand ...

    Popular withFoodiesLocalTrendsters
  • 13

    Wrigley Field

    163 reviews

    Chicago's Wrigley field hometown fans, are some of the most gracious, fun, and pleasantly welcoming home field fans this sporting Cardinal fan has ever encountered. Thank YOU Cubbie fans for such a fantastic time and GREAT experience!

    Popular withLocalHistoryTrendsters
  • 14

    Emporium Arcade Bar

    5 reviews

    Pinball takes me back. So does Ms. Pac-Man, Dig Dug and Donkey Kong and basically anything NeoGeo. All of these things were found here! As an adult, I can really appreciate the nostalgia that occurs when I walked into Emporium. A gem in Logan Square, and certainly a must do if you take video games with your whiskey.

    Popular withBackpackersNightlifeTrendsters
  • 15

    The Crocodile

    2 reviews

    Can't decide whether you're in the mood for a bar or a club? Crocodile is the best of both worlds with the typical bar scene happening upstairs and a full-on dance party erupting just a staircase below. Fishbowls keep the party going all night, while free personal pizzas with every drink purchase soak up some of the alcohol and serve ...

    Popular withTrendstersNightlifeBudget
  • 16


    4 reviews

    Delicious food and drinks. I highly recommend getting a whole animal (particularly the pig) cooked for a big group celebration. PS- On Wednesday nights they turn the upstairs into a speakeasy!

    Popular withFoodiesTrendstersNightlife
  • 17

    The Hideout

    4 reviews

    One of the city’s finest “hidden” gems, the Hideout is located on an industrial stretch that’s also home to a garbage-truck parking lot and a municipal-car gas station. The bar is basically a 100-year-old balloon-frame house that serves booze out of its living room, and hosts comedy sets and concerts out of the back. In fact, this is a spot ...

    Popular withAdventureTrendstersHistory
  • 18

    Empty Bottle

    3 reviews

    The Empty Bottle has been booking envelope-pushing musical acts since 1992, and has established itself as a mecca for Chicago’s bohemian, music-loving community. From bluegrass to bounce music, nearly every genre has been represented here, and the venue has also popped up at #12 on Rolling Stone’s list of The Best Clubs in America. Monday-night shows are often free, and ...

    Popular withBudgetTrendstersStudents
  • 19

    Maude's Liquor Bar

    3 reviews

    Favorite restaurant in the city! The food is amazing every time, great French 1920s ambiance and drinks made to perfection!

    Popular withFoodiesTrendstersDesign
  • 20

    The Owl

    2 reviews

    Located in Chicago's up-and-coming Logan Square neighborhood, The Owl is a great 4am (5am on Saturdays!) spot for those situated on the West Side of the city. True to its name, the bar is covered in owls of all shapes and sizes and fills up with the type of night owls who like to drink craft beer and get down ...

    Popular withTrendstersNightlife
Pick Dates for Best Prices:Compare across,, and many more
Fetching recommendations for your next adventure ...