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  • 1

    The Magnificent Mile

    North Michigan Avenue, Chicago, IL 60611
    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 withLuxuryFamiliesBusiness
  • 2

    Violet Hour

    1520 N Damen, Chicago, IL 60622
    20 reviews

    Incredible speakeasy bar that's door is hidden within a brightly colored painted wall mural! The Romeo and Juliet is my favorite drink here! Must come if you love cocktails!

    Popular withTrendstersLuxuryNightlife
  • 3

    John Hancock Center

    875 North Michigan Avenue, Chicago, IL 60611-1779
    114 reviews

    The John Hancock Center is a "must see" in Chicago. Visitors have the opportunity to go up over 90 floors to an observatory that offers spectacular views of the city and Lake Michigan. After some scenic photo taking, visitors can head over to the Signature Room on the 95th floor for a nice romantic dinner in the dining room or ...

    Popular withFamiliesLocalLuxury
  • 4

    Signature Lounge

    875 North Michigan Avenue, Chicago, IL
    9 reviews

    Enjoy the view that you'd get from the observation deck but do it with a cocktail. A really lovely bar offering one of the best views in the city. Yes, it is touristy but it really is special.

    Popular withDesignTrendstersLuxury
  • 5

    Downtown Chicago

    E Wacker Service Dr, Chicago, Illinois
    37 reviews

    One of the great urban centers of the United States. The architecture is lovely, the people are friendly, and the food is excellent. The location next to Lake Michigan makes this a truly special place -- just avoid it in the winter.

    Popular withLuxuryLocalDesign
  • 6

    Goodman Theatre

    170 N Dearborn St
    10 reviews

    Chicago has a spectacular theater scene that rivals NY and this this is the premier theater in the city. Less commercial than Broadway. What theater should be.

    Popular withLocalLuxuryDesign
  • 7

    Old Town Pour House

    1419 N Wells St, Chicago, Illinois, United States
    2 reviews

    Old Town Pour House honors its namesake by pouring up one of the biggest drink selections in the city. With over 90 beers on tap, this is a brewski-lover's heaven. Go with a flight to sample more flavors at once and don't miss the food menu by Executive Chef Paul Katz, particularly the slow roasted pork belly with blueberry bbq.

    Popular withFoodiesLuxuryNightlife
  • 8

    Old Town Art Fair

    1763 N North Park Ave, Chicago, Illinois
    2 reviews

    A great reason to explore Old Town and always a fantastic weekend. The city really comes together for this one and it is one of my favorite festivals in Chicago.

    Popular withLocalLuxuryTrendsters
  • 9

    Macy's State Street

    111 North State Street, Chicago, IL
    16 reviews

    Worked at this Macy's as a seasonal sales associate and did all of my Christmas shopping here that year. Outstanding customer service, great products, clean and orderly store, big savings during the holidays with your Macy's card.

    Popular withFamiliesLuxuryBusiness
  • 10

    The Merchandise Mart Building

    222 Merchandise Mart Plaza, Chicago, IL 60654-1001
    8 reviews

    One of the best home decor / design centers in the US. It is massive. Less a tourist attraction than a place to find inspiration if you are on the verge of embarking on a decorating spree.

    Popular withLuxuryBusinessTrendsters
  • 11

    Vertigo Sky Lounge

    2 West Erie, Chicago, IL
    4 reviews

    Located at the top of the chic Dana Hotel, this is a fabulous place to lounge and take in the incredible city views of Downtown Chicago. The 26th floor rooftop lounge has both an indoor and outdoor space, though I'm sure the outdoor area gets much less love in the cold weather months which seem to last almost all year ...

    Popular withLuxuryTrendstersNightlife
  • 12

    Barneys New York Chicago

    15 East Oak Street, Chicago, IL
    2 reviews

    My favorite department store in Chicago. Smaller than NY but well-curated and more stylish than Saks, Nordstrom, or Bloomies. As close to NY as you will get in Chicago.

    Popular withLGBTLuxuryTrendsters
  • 13

    Lyric Opera of Chicago

    20 N Wacker Dr
    6 reviews

    Lovely opera house. The best place for opera in the city. It isn't the Met but is still a wonderful venue that attracts incredibly talented performers.

    Popular withLocalLuxuryDesign
  • 14


    520 N Michigan Ave # 328, Chicago, IL
    7 reviews

    A good #2 for men in Chicago. The men's section is a bit conservative but is a great place to pick up basics -- and, occasionally, that special jacket, sweater or pair of shoes.

    Popular withLuxuryDesignBusiness
  • 15

    NoMI Garden

    800 North Michigan Avenue
    1 review

    Great cocktails in an outdoor setting. Perfect in summer. Has been around for a while but still very swank.

    Popular withLuxuryOutdoorTrendsters
  • 16

    Water Tower Place

    835 N. Michigan Avenue, Chicago, IL 60611-2104
    27 reviews

    It may be iconic but this is still a mall. Nice but a bit past its prime.

    Popular withLuxuryFamiliesLocal
  • 17

    Gold Coast

    1300 N. Lake Shore Dr., Chicago, Illinois
    4 reviews

    This upscale neighborhood has nice residential architecture and is in close proximity to the lake and the best shopping. Very little to really draw tourists. If you are interested in the architecture, walk down Astor.

    Popular withLuxuryFamiliesBusiness
  • 18

    Navy Pier Ferris Wheel

    600 East Grand Avenue, Chicago, IL 60611-3426
    55 reviews

    The first Ferris wheel was torn down shortly after the World’s Fair in 1893, but its spirit lives on in this smaller replica on the site of the original. Although this Ferris wheel is nearly half the size and can carry only 240 people (compared to the 2,160 people carried by the original), it is one of the Navy Pier’s ...

    Popular withFamiliesAdventureLuxury
  • 19

    Architecture River Cruise

    333 North Michigan Avenue, Chicago, IL 60601-3700
    35 reviews

    Home of the skyscraper, taking the time to appreciate the city's architecture is a major thing to do when you're in town. There are a lot of boat tours to choose from, but your money is best spent on the slightly more expensive tour run by the Chicago Architecture Foundation. With experienced, knowledgable staff, you'll walk away tons of fun ...

    Popular withHistoryLocalDesign
  • 20


    955 West Fulton Market, Chicago, Illinois 60607, United States
    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 withTrendstersFoodiesLuxury
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