Chicago, the “Jewel of the Midwest,” known for its deep-dish pizza, jazz music, architecture, and …notorious mobsters. Chicago is the third largest city in the United States. Unlike New York and Los Angeles, you can get a good feel for the city during a weekend getaway. Sometimes called The Windy City (lore says its for its politicians as well as its weather), the city’s entire east side is bordered by Lake Michigan and offers miles of waterfront walking.
Get settled into your accommodations and then head out to dinner at Giordano’s for some famous deep-dish pizza. They have many locations, so look up which is closest to your hotel or evening plans. Gino’s East and Lou Malnati are also local favorites for deep-dish. Save room for pizza dessert!
After dinner, I recommend heading to The Green Mill Cocktail Lounge (4802 N Broadway, Chicago, IL 60640) for a live jazz performance. This uptown lounge was notorious Chicago gangster Al Capone’s old stomping ground.
Saturday: “The Loop”
Start your morning with the Chicago Architecture Foundation’s river cruise (you can start at either of two locations, I recommend starting at 401 N Michigan Ave). This is a cool and enjoyable way to see the city. The river tour guides provide a nutshell of the city’s history in addition to the city’s famous architectural sites. The price is roughly $45, and tours begin every 20 minutes.
After the tour, walk over to Millenium Park to see the much-photographed “Bean.” Millennium Park is located in the heart of the city, and is bordered by many cultural and art institutions. Check out the Tiffany Glass dome in the landmarked Chicago Cultural Center (78 E Washington St.), which was built in 1897 and is open to the public at no charge. Also nearby is the former Marshall Fields Flagship store, which is now a Macy’s (111 N State St). Get a snack and enjoy spectacular views over Millenium Park at Cindy’s (12 S Michigan Ave), located on the 13th floor of the 1893 Chicago Athletic Association Hotel.
Head up to the Old Town/Goldrush neighborhood to catch a 4:00 pm comedy show at The Second City (1616 N Wells St.), which has launched the careers of many celebrity comedians such as Tina Fey, Stephen Colbert, and Bill Murray. After the show, get a happy hour drink and peruse the exquisite furniture offerings at Restoration Hardware, now known as RH (1300 N. Dearborn St.) which is located in an old arts club.
Get some dinner in the Lakeview East neighborhood. Both N. Halsted St and N. Clark St offer a number of great dinner and debauchery locations. N. Halsted is the main strip in Boystown, the historical LGBTQ neighborhood, while N. Clark St, in the Lakeview neighborhood, is geared more towards a younger crowd and Cubs baseball overflow, since it runs south of Wrigley Stadium.
Sunday: Evanston, IL
Start your morning by taking the metrorail to Evanston. Get a coffee and pastry from Hewn Bakery (1733 Central St, Evanston, IL). Spend an hour touring downtown, which has many interesting galleries, small businesses, and museums. Walk over to Northwestern University’s campus, and don’t and forget to check out the waterfront views in the Lakefill section of the campus. After Northwestern, get a two-mile ride to the architectural gem that is Baha’i House of Worship (100 Linden Ave, Wilmette, IL 60091). You can ogle the lace-style details for hours!
For those who do not want to make the roughly one-hour train ride to Evanston, the neighborhood of Ravenswood in Chicago is quaint and offers much to do. It has an old fashioned apothecary. Each fall, Ravenswood sponsors a superb Apple Festival in Lincoln Square. I recommend checking it out if you have a chance.
Cheers to a great weekend in Chicago!
Thank you to Emma, Katrina, Elizabeth, and Jimmy for showing us around your city! Thank you to Meghan and Sarah for exploring with me 🙂