Take a Long Weekend to Chicago: You Can Do A LOT With This Check List

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Chicago is a fabulous city to explore and obviously well known for its blues bars/clubs and music. We don’t really cover that here but below is a great list of places to explore such as beaches and shopping, as well as places to stay, eat and drink.

Let’s start with the fact that you’re probably going in the summer, spring or fall, rather than when it’s below zero and snowing. When the weather is great, Chicago is wonderful, when you can take advantage of the numerous places you can hang outside and better yet, lounge outside.

The Beaches:

12th Street Beach: on the island near the Adler Planetarium, the uncrowded beach feels like its miles from the city.

North Avenue Beach: just beyond Lincoln Park, you can get amazing skyline views and see a beach house that looks like a boat.

63rd Street Beach: this is a historical beach, where there’s a bath house build in 1919 and you can also take in concerts and volleyball.

Osterman Beach: this is a boardwalk which offers a shallow wading area. Great place to take kids.

Montrose Beach: this stretch is where a lot of the locals hang out and party, so imagine a sighting of dogs, grilling and lounging about.


Original Pancake House on 22 East Bellevue Place.

Frontera Grill on North Clark Street, an upscale Mexican cantina.

Portillo’s for Chicago hot dogs.

North Pond for brunch, which is a James Beard award-wining eatery inside Lincoln Park. They use local, organic food here and be sure to check out their crispy trout.

Lou Malnati’s Pizzeria for pizza, which is known for its light, flaky “Buttercrust” topping, complete with thick sauce and mozzarella.

Girl & the Goat is helmed by top chef winner Stephanie Izard, and is one of the hottest restaurants in town.

Leopold is a Belgian-style bar where you can relax and take in the Flanders cocktail of the Leopold Brothers, boutique gin, elderflower liqueur, housemade lemon bitters and basil syrup. (yum).

Aria Restaurant in the Fairmont Hotel near Millennium Park. It’s an Asian restaurant with a view of the park that offers delicious tuna tartare and short ribs among many other savory treats.

Moto to splurge on Homaru Cantu and Ben Roche’s 20-course (yup, 20 courses) tasting menu, printed on wafer-thin brioche with cashew butter and reduced blueberry syrup. (this is enough to make me want to go alone). Then we get into the pureed corn bread and parsley powder, and more.

Other Chicago Attractions:

Green City Market, which is a massive farmers market with vendors that tout everything from carrots, cheese and wheatgrass juice and other delicacies.

Fulton Market, a working meat market by day but it is also full of lofts and warehouses housing art and design studios, galleries and boutiques where artists hang out and work.

Wicker Park: once a working class neighborhood, it is now a haven for creative 20 something year olds who are there to hang out and take in vintage clothing shops and boutiques. They have high-end jewelry like Alexis Bittar as well.

Skydeck at Willis Tower. You can take in an exhibit here as well as a short film about the city’s architectural and mercantile history. Head up to the 103rd floor for an incredible view.

Grant Park – check out the waterworks at iconic Buckingham Fountain and then head north to grab a Ferris Wheel ride at Navy Pier.

Millennium Park – go to Anish Kapoor’s Cloud Gate, which is known as the “Bean.”

Flat Iron Arts Building at the intersection of Damen and North Avenues are lined with artist studios open to the public.

Lincoln Park Zoo, home to 1,200 species and an antique carousel.

LuLu’s at the Belle Kay for shopping for accessories, hats, shoes, and jewelry.

Chicago Architecture Foundation Boat Tour from the southeast corner of Michigan Avenue Bridge at Wacker Drive

Chicago Cultural Center on East Washington Street

The Water Tower on North Michigan Avenue.

Gold Coast & Magnificent Mile for shopping. Marked by the Water Tower, you can explore Chicago’s shopping mecca.

Margie’s Candies in Bucktown, which opened in 1921 and exudes history and kitsch. Try the coconut ice cream sundae.

Hotels & Places to Stay:

Elysian Hotel, a posh unmarked villa set back from the street to make you feel as if you can escape from the city noise. Rooftops are planted with grass to absorb rainwater and provide insulation. The foliage makes for an urban landscape like none you’ve ever seen.

Fairmont Hotel near Millennium Park which has a great Asian restaurant called Aria. See above under food.

The James Hotel, which has original artwork like the suitcase installation in the lobby. You can get an amazing king loft here if you’re willing to splurge, which has dark wood furniture and shag carpeting for a real “at-home” feeling.

Hotel Palomar has titanic jetted tubs, which is included if you sign up for one of their Surf’s Up package (I have never done). It is located on 505 North State Street in Chicago.


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