Published: January, 2018
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Chicago, Illinois

Windy, charming perfection in the Midwest.
— Cynthia Pillsbury
  • More about your oliver guide:
  • Trip type: Family, City
  • Activity level: easy
  • Ideal length of trip: 3 days with kids

to & from

From any major city fly into Midway or O’Hare. No need to have a car; uber or walk everywhere!

Where to Stay

Chicago Athletic Association (CAA): built in 1893 and recently restored, is a perfect place to call home whether you are with your kids, friends, husband or alone! The location is across from Millennium Park which is central and provides a great view.

Where to Eat and Drink

  • Cindy’s on the CAA Rooftop: Great food with amazing views, great for lunch, dinner and/or a nightcap on the expansive terrace.
  • Shake Shack: Perfect spot for lunch with kids before you hit the town, can’t find a better burger and fries and shake, imported from New York and it fits right in!

What to Do

Museum Mile: skip the Planetarium, (unless you have a budding astronomer) and spend time at the She’d Aquarium; make sure to buy tickets to a sea animal experience. The Field Museum (Natural History) is also worthwhile.

Millennium Park: Climb the wall, putt putt golf, stroll through the herb and flower gardens, take in star-lit concert or movie and rent bikes in the park and bike along Lake Michigan.

The Art Institute: It’s a big, overwhelming museum so with kids we focused on the traveling exhibit and headed to the basement to see the “miniature rooms” which captured my kids’ attention and mine; incredible to see dollhouse scale home decor from the past 200+ years.

Architecture Tour by Boat: These tours by boat are relaxing, fun and interesting and you can get a glass of wine while your kids are engaged in an entertaining oral history lesson of the city’s incredible architecture.

inside scoop

  • Water Taxi’s are a really fun way to visit Museum Mile to the Navy Pier. You can buy tickets before you board.
  • If you go to the Sky Deck in the Willis Tower make sure you pony up and buy the FAST TRACK pass- it is not worth the time standing in the never ending maze. With the Fast Track you can zip up and experience the Sky Deck but not spend all day getting to it! Not sure it’s worth it if you have anyone with a fear of heights… or crowds.

Chicago, Illinois - Suggestions from the Oliver Community

  • Sabrina Eliasoph Says

    We loved the “>360 Chicago experience on top of John Hancock building. It is yet another observation deck, but they have an experience called TILT, in which they literally tilt out in a glass box at a 90 degree angle over Michigan Avenue. Hang on, as the vertigo sensation is wild!

    There is no better burger in Chicago than Au Cheval ( Long lines for lunch– we waited over an hour for a table but it was well worth it. Cute ambiance insanely awesome burgers

    Do not miss Pacific Standard Time (, another awesome new hot spot restaurant. Such yummy sophisticated California-cuisine, but also a great, open airy space.

    While some might think of Le Colonial ( as a place that used to be cool, in Chicago going there for a bar is still very on point. They in fact recently moved the location and the open-air bar with French Vietnamese fare and vibes was hopping! The cocktail lounge is beautiful – a great place for a drink if you’re shopping on Oak Street.

    While the classic Art Institute is a must, don’t overlook the MCA – Museum of Contemporary Art- ( I saw the Virgil Abloh exhibit that was so thoughtful and fabulously curated. The permanent collection is VERY impressive and it’s an easy location, a couple blocks off of Michigan Avenue.

    I have a soft spot for any Ralph Lauren restaurant and the RL Grill in Chicago is just an awesome place to pop in for a yummy meal and a drink, especially if you are shopping on Michigan Avenue. When seeking a good Bloody Mary, paired with a tasty burger, those classy tartan plaid fabrics, oil paintings of polo matches and horses, and dark walls are just perfect.

    Calling all adventurous eaters! The Girl and the Goat ( is delicious, daring, and dare I also say, not for everyone! If you like very simple meats and you plain foods, skip this place. However, if you’re up for some goat, pig face, duck tongue, and other interesting menu offerings, you will love the food. The menu was a little tricky for our kids but Mark and I thought food was fantastic. And the place was packed!

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