36 Hours in Chicago

posted by Maressa Levy on August 23, 2013

Cloud Gate by Ryan Bailey

Chicago, Illinois -- From Lollapalooza and Wavefront to the upcoming North Coast and Riot Fest, Chicago is quickly becoming a go-to destination for music lovers. Below are some of our favorite spots in this lakeside city, from restaurants to museums and parks.

Day One

3pm: Head over to Navy Pier
600 East Grand Avenue
This 50 acre pier is a smorgasboard of entertainment, with shops, dining, bars, and museums lining the walkway. During the summer, take a trip off shore on one of many sightseeing and dining cruises, or head to Pier Park for a ride on the 150-foot Ferris wheel. If you don't have time to visit one of its attractions, it's just as pleasant to take a walk along the iconic pier, which was constructed in 1916.

4pm: Head to one of Chicago's beaches
Just a short walk from Navy Pier is the Ohio Street Beach, or visit the beautiful Oak Street Beach, which offers remarkable city views. While you're there, stop in the Oak Street Beach restaurant, open from Memorial Day through Labor Day. Enjoy watermelon salad, fish tacos, Piña Coladas, and buckets of sangria beachside and soak up the sun alongside Lake Michigan.

7pm: Chicago-style pizza at Lou Malnati's
805 South State Street
While Lou's is a chain, Chicago Magazine ranks the eatery among Chicago's best for traditional deep dish pies. Conveniently located near Grant Park, this location also features a full bar as well as gluten-free pizza options. Opt for "The Lou," a deep dish pizza topped with spinach, mushrooms, and tomatoes and covered with three varities of cheeses.

Day Two

10am: Grab brunch at Rockit Bar and Grill
22 West Hubbard
In addition to Rockit's unique food offerings (Oreo cookie pancaked with chocolate syrup or cinnamon raison french toast, anyone?), Rockit offers a $6 gourmet bloody mary bar with more than 18 toppings and incredients, including shrimp and toothpicks of ham and cheese. $6 mimosas and a live band sweeten the deal.

Noon: Explore Grant Park
337 E Randolph St
This massive 319 acre park is known as Chicago's "front yard," and houses the Buckingham Fountain as well as Millennium Park, the Art Institute of Chicago, the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium. Perhaps most notably, Grant Park is also home to Chicago festival Lollapalooza, which attracts thousands of music fans to the park annually.

Be sure to check to out Cloud Gate, a giant sculpture better known as "The Bean" located in the smaller subset Millennium Park. Contructed from 2004-2006 by British artist Anish Kapoor, Cloud Gate acts as the centerpiece in the city's AT&T Plaza, and the city's skyline is uniquely distorted on the bean's reflective surface. While this area is likely to be tourist-heavy, it's worth it for a look at this beautifully polished piece of art. Walk underneath the bean's 12ft tall arch and look up to see ununusual angles and warped reflections.

2pm: Take a break indoors at the Art Institute of Chicago
111 South Michigan Ave
Nestled within Grant Park, the Art Institute of Chicago houses an impressive permanent collection of Impressionist and Post-Impressionist paintings, early 20th-century European paintings and sculptures, contemporary art, Japanese prints, and photographs. Whether you decide to spend the day or just a few hours at the Institute, this storied museum is sure to have something to entice even the most fickle museumgoer.

4pm: Stop for a late lunch or early dinner at Terzo Piano
159 East Monroe Street
Located inside the Art Institute, Terzo Piano uses locally sourced ingredients from vendors within 150 miles of the restaurant to create nutritious seasonal meals and beverages that are as healthy as they are delicious. While Terzo can be pricey, the eatery provides beautiful park views, managing to bring the outside in with large windows and simple décor. Patrons can also dine al fresco on the restaurant's Bluhm Family Terrace, and enjoy a cocktail, fresh juice, or house made soda overlooking Michigan Avenue.

6pm: Get a bird's eye view of Chicago from the Skydeck
233 South Wacker Drive
Open 365 days a year, no visit to Chicago is complete without checking out the Skydeck. Housed in the tallest building in the western hemisphere and the third tallest in the world, the Skydeck's glass-enclosed Ledge extends just over 4 feet from the building at 1,353 feet on the 103rd floor. The deck is open until 10pm April through September and until 8pm October through March, and keep in mind last entry is 30 minutes prior to close.

8pm: Dinner at Davanti Enoteca
1359 West Taylor Street
Located in Chicago's Little Italy, this rustic yet elegant restaurant features a 45-seat rooftop deck. The small 10-seat bar has only two taps - one for local Chicago-brewed beer, and the other for the restaurant's house vodka. Opt for formaggi + salumi to take your pick of cured meats and fresh cheeses, or order a slew of small, sharable plates to sample a bit of everything.

Day Three

11am: Quick, casual breakfast at Corner Bakery Café
444 North Michigan Avenue
Stop in for fresh cup of coffee and a bakery treat (try the Cinnamon Creme Cake), or sit down and enjoy a freshly-prepared omelette, panini, or yogurt parfait. If you're in the mood for something a bit more filling, try one of the bakery's 137 corner combos, all less than 600 calories.

1pm: Shopping on Magnificent Mile
Michigan Avenue
From giant shopping centers to unique boutiques and designer studios, Magnificent Mile is stocked with shopping options for every taste. Whether you desire shoes, apparel, luxury dog collars, books, home furnishings, or groceries, you'll find it on this fully-stocked strip. For a full directory of the Mile's shops, head to their official website.

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See Also:

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