Chicago had been on the top of my travel wish list for a while, and for our fifth wedding anniversary, we decided to spend a long weekend in the “Windy City.”
September was a perfect time to visit Chicago because the weather was outstanding and the city was not overwhelmingly busy. For a first visit, three full days is an adequate amount of time to obtain a solid overview of Chicago. We covered quite a bit of ground, while still leaving places to explore during a return trip.
If you’re considering a quick getaway to Chicago, I wanted to share my suggestions for how to spend a fantastic long weekend in Chi-town! Happy exploring!
The A-Lyst for a First Visit to Chicago
Explore Chicago’s Street Art
There is definitely something to be said about the amount of amazing street art in the city of Chicago. I was so blown away by the level of detail in the artwork that we ended up spending an afternoon exploring various neighborhoods, while on a hunt to spot different murals. A few of my personal favorites included the “Greetings to Chicago” postcard sign (created by Victor Ving & Lisa Beggs and located at 2236 N. Milwaukee Avenue), the Heart Emoji wall (printed on a garage door and located at 1820 W. Webster Avenue), and the Flamingo wall (the exterior of the Flamingo Rum Club at 601 N. Wells Street). I’d recommend researching the various murals and making a map of your personal “must-see’s,” keeping in mind that many are geographically spread apart, so renting bikes or using UBER is your best bet!
This 18-mile scenic pathway offers the most picturesque view of both the Chicago skyline and glistening waters of Lake Michigan. Beginning at Ardmore Street and ending at 71st Street, the paved trail is a great way to get in some exercise while exploring the city. For a short ride, I’d recommend renting bikes through Divvy Bikes, which has multiple outposts along the path, or if you plan on going the full distance, I would opt for a bike rental at Bobby’s Bike Hike or Lakeshore Bike. The trail is shared with walkers, joggers, and rollerbladers, which initially made me nervous since I am not the strongest biker, but the area is wide enough to comfortably accommodate everyone. Additionally, there are many restaurants and beaches along the way, so you easily spend a day leisurely biking and exploring the lakefront.
Take the Chicago Architecture Foundation River Cruise
Chicago’s 90-minute architecture river cruise was by the far the most highly recommended activity, and after taking it, we totally understood why! You will learn all about the city’s different skyscrapers (there are many and each one has a story!) as well as interesting facts about Chicago. I would suggest booking your cruise on the first day that you are in the city, as it’s an excellent way to identify all of the amazing buildings you will see over and over again during your visit.
Imbibe Rooftop Cocktails 
I love how many awesome rooftop lounges there are in Chicago! Coming from Boston where we keep the majority of our imbibing on the ground, it was fun to explore the city’s various bars with skyline views. Cindy’s Rooftop in the Chicago Athletic Club had great drinks with a stellar vantage point to see the Cloud Gate and Millennium Park, while the J. Parker rooftop affords you unobstructed views of the lush Lincoln Park and Lake Michigan.
Eat Chicago Hot Dogs and Deep Dish Pizza
If you’re someone who likes to enjoy the signature food of every place that you visit, than enjoying a Chicago-style hot dog and famous deep dish pizza is a must when exploring the Windy City. Chicago’s hot dogs are topped with yellow mustard, white onion, green relish, sport peppers, tomato, celery salt, ketchup and a pickle, and then served on a poppy seed bun. Portillo’s is tourist-central and always has a very long wait, but I’ll hand it to them, they make a good hot dog! Everyone associates Chicago with deep-dish pizza, so we had to try some before leaving the city. Growing up near New Haven, Connecticut, which is a fairly famous “pizza city,” I am pretty discerning when it comes to pies, so I can’t say I was THAT blown away by the deep-dish that I tried, but I am still glad I had it. The go-to touristy pizza spots in Chicago are Lou Malnati’s, Giordano’s, and Gino’s East.
Visit Monet, Andy Warhol and Grant Wood
The Art Institute of Chicago is one of the oldest and largest art museums in the United States and houses around 300,000 works. The museum offers a helpful tip sheet on what to see if you have limited time, so following their advice, we were able to enjoy top works by Monet, Van Gogh (his self-portrait is there), Andy Warhol (“Liz #3”, an Elizabeth Taylor piece, which was recently donated, lives there) and Grant Wood (his famous American Gothic painting is in the museum). This museum is consistently top-rated, so if you’re up for adding an educational component to your weekend in Chicago, it’s worth a visit!
Let’s just say, Michigan Avenue definitely stimulates the economy. Almost every major store can be found on this 5th Avenue-esque shopping street and if you’re visiting from a place that doesn’t have all of the top designer boutiques, it’s fun to check them out. Beyond the fashion, I actually enjoyed the beautiful architecture and hidden parks off of Michigan Avenue. We found a gorgeous ivy-covered church and courtyard (the Fourth Presbyterian Church of Chicago) and the design of the Chicago Water Tower looked like a castle in the middle of the city. I would recommend strolling down North Michigan Avenue and connecting to North Rush Street and East Oak Street where you will find friends like Hermès, Saint Laurent, Barney’s, and Prada as well as many excellent eateries.
Stroll through the Gold Coast
In whatever city we visit, I like to explore the different neighborhoods, and in Chicago, the tony Gold Coast district was definitely my favorite. Gorgeous houses, all with their own unique style of architecture, lined the streets, and we couldn’t help but stop and take photos of our favorites! The entire Gold Coast has been part of the National Register of Historic Places since the late 1970s, and North Astor Street as well as North State Street had some pretty remarkable older homes. If you also enjoying leisurely strolling and “house-hunting,” this is a great neighborhood to do it!
Lunch at 3 Arts Club Cafe (and Furniture Shopping!)
For fans of Restoration Hardware’s crisp yet elegant aesthetic, 3 Arts Club Cafe is your dream restaurant. In fact, you will probably want to move into it. Located in the center indoor courtyard of RH Chicago, the space boasts high glass ceilings, a gorgeous trickling fountain, and sparkling chandelier…in other words, it’s stunning! This posh Gold Coast eatery is perfect for a lunch with friends, afternoon cocktails, or fuel-up mid-furniture shopping. I highly recommend asking for a table near the fountain and ordering the Truffled Grilled Cheese; you won’t be disappointed! 1300 N. Dearborn Parkway, Chicago, IL 60610
Outfit Details:
Biking the Lakefront Trail:
Top: J.Crew Boyfriend Shirt in Vintage Red Plaid
Jeans: Frame Denim Le Skinny de Jeanne Jeans in Columbia Road
Shoes: Sam Edelman Greta Thong Sandal in Jute
Chicago Street Art:
Dress: Joie Norton Dress (out of stock; similar here)
Shoes: Chanel Rhinestone CC Thong Sandal (similar here)
3 Arts Club Cafe:
Dress: J.Crew Short-Sleeve Cotton Shirt Dress
Chicago Riverfront:
Top: Royal Blue Ruffle Off-the-Shoulder Blouse
Jeans: FRAME Le High-Rise White Skinny