Things To Do
Soak up Summertime in Chicago!
Whether this weekend is your first or hundredth time in the Windy City, we’re confident these bucket list activities will make you fall in love with Chicago like never before. While we know you’re here to celebrate our nuptials, we hope you’re also able to take advantage of the weekend and summertime Chi!
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Walk along the 606 Trail in Logan Square/Humboldt Park
Get off at the Milwaukee Ave exit for coffee at Ipsento and great burgers at either Small Cheval or The Stop Along; get off at the Spaulding Ave exit to enjoy coffee at Dayglow Coffee and beer at Orkenoy (both in the Kimball Arts Center building). -
Take an architecture boat tour on the Chicago River and see downtown from the river (plus, learn about Chicago’s rich history in architecture)!
Both the Chicago Architecture Foundation and the Wendella boat company offer tours, but we think the best tour is definitely with the Chicago Architecture Foundation onboard their boat Chicago’s First Lady. Tickets are about $50 and so, so worth it! For people who don’t care about architecture, you will now (it’s also not just about the architecture…it’s about the history and the pretty views!). -
Walk along the Riverwalk and the lakefront.
The Riverwalk is right along the river downtown and below traffic; it’s such a cool way to see the city.
The lakefront is also beautiful. If you want to go for a long run or walk on Saturday morning, definitely go on the lakefront trail! Chicago also has a rentable bike program, the divvy bikes. Considering renting a divvy and biking along the lakefront! For great views of the city, head up to Montrose Beach or down to Promontory Point or Adler Planetarium. This weekend just so happens to be Chicago’s Annual Air and Water Show. Low-flying planes will dazzle along the lakefront and the sights and sounds of the jets can be enjoyed from all over Chicago. -
Craft your own pizza tour.
For deep dish (a Chicago specialty), we recommend Pequod’s or Lou Malnati’s. For Neapolitan style, we recommend Spacca Napoli or Paulie Gee’s (Wicker Park or Logan Square locations). For pan or Detroit style, we recommend Paulie Gee’s (Logan Square location) or Pizza Friendly Pizza. -
Get a drink at Cindy’s Rooftop, a bar located at the top of the Chicago Athletic Association (right across from Millennium Park and The Bean).
Cindy’s has a gorgeous bar and great drinks. The outdoor patio overlooks Millennium Park, The Bean, Grant Park, some of downtown, and the lake. -
See a comedy show at the legendary Second City.
Not on Saturday night, though…you’re busy at that time. You have our permission to go on Friday night if you like. They also have Saturday and Sunday matinees! -
Sip craft beers and ciders at Eris Brewery & Cider House.
This is where we spend a lot of time in the winter, but they also have a great outdoor patio. Eris is also home to some of the world’s best fried pickles. Quick plug for supporting a small, woman-owned business, too! -
Have a picnic or some reading time in Palmer Square Park.
This park is minutes from our house, and we love to go there. It has some cool art and a lot of green space. Consider grabbing a slice of pizza from Paulie Gee’s (see #5 above), a burger from Mini Mott, the Werp Farm lettuces from Lula Cafe, a sandwich or pastry from La Boulangerie, or some noodles from Trike or Three Wheel beforehand (for the picnic part). -
Craft your own ice cream tour.
Our favorites include Miko’s Italian Ice (also in our neighborhood and very close to Palmer Square Park – see #8 above), The Freeze, Jeni’s Splendid Ice Creams, Margie’s Candies, and Pretty Cool Ice Cream. -
If it’s a rainy day, head to the Chicago Athletic Association (CAA) to check out their multi-story, very cool restored spaces.
The Cherry Circle Room, The Game Room, and The Drawing Room each boast their own theme, great drinks, and cool ambiance (reservations may be helpful but are not always necessary). Finish your stay at the CAA with a drink at Cindy’s Rooftop (see above). -
Walk through Millennium Park and Grant Park.
This is where The Bean is located along with the Pritzker Pavilion, Buckingham Fountain, and luscious gardens. It’s also very close to the lakefront. In the summer, there are often free concerts happening throughout the parks, so keep an ear out! -
Take advantage of Chicago’s multitude of excellent museums.
From the Art Institute to the Museum of Science and Industry, Chicago’s museums are not to miss (especially for you museum buffs!). The Museum of Contemporary Art is also really cool and in a great spot in the city – Michigan Ave’s Mag Mile! If you’re into aquariums, the Shedd Aquarium gives you a super cool view of downtown, is right on the lake, and is home to what was once the largest fish tank in the world. -
Visit the Chicago Cultural Center (it’s free!).
The Cultural Center used to be the public library but now holds multiple free art exhibits usually about Chicago and its people. The legendary Tiffany Dome is also housed there (made of Tiffany glass). Not to miss! -
Take a walk through the Garfield Park Conservatory.
We also spend a lot of time in the winter here because it’s warm and filled with lush, rare vegetation. Although it’s a ways west, if you’re a plant and flower aficionado, we couldn’t recommend this spot more. -
If you’re up for an adventure (aka a small trip), travel down to Hyde Park.
The University of Chicago’s campus is beautiful, and it and Washington Park are right next to the Museum of Science and Industry. There’s also a great coffee shop on the campus called Plein Air Cafe. There are also some great restaurants on 55th St. -
Stroll through Lincoln Park.
From the zoo (free!) to the lakefront access to the hidden sculptures to the conservatory, you’re sure to find something wonderful in Lincoln Park, almost all of which is outside. -
Get a Chicago-style hot dog at one of the many historic stands around the city.
We like Red Hot Ranch in Logan Square, but all serve the legendary Vienna Beef with accoutrements. Don’t you dare add ketchup, and make sure you ask for plenty of sport peppers.