Traveling the big cities alone can be exhilarating – and Chicago is no exception. Whether you’re a solo traveler or alone in Chicago on business, there’s plenty to do and see. Here’s a perfect weekend itinerary for solo travelers looking for a mix of Classic Chicago sightseeing and neighborhood charm.
Day 1: Downtown Chicago + visits
On your first day of solo travel, dive into Chicago’s Iconic Architecture and the magic of the downtown Loop.
To eat lunch
Start the day with brunch at Althea for an all-vegan, chef-led weekend brunch. Located just off Michigan Avenue on the 7th floor of Saks 5th Avenue, this is the perfect place to start your day. The view, intimate space, and full bar make this a perfect spot for solo travelers.
Want something quick? Try Stan’s donuts for delicious specialty donuts or Goddess and Baker for a quick breakfast sandwich and coffee.
Look at the landscape
A free walking tour is a fun way to see the city center and possibly meet other people traveling alone.Free walking tours offers several options, including a Loop/Millennium Park tour and a Chicago Riverwalk tour.
Want to explore on your own? Here are some must-haves for your list:
Solo travel advice: Bring headphones, a book or a newspaper to dine alone or talk to people around you. Bring a tripod to take photos of yourself and the sights. I also recommend downloading a few episodes of your favorite podcast to listen to while visiting and shopping.
To eat lunch
Chicago’s downtown Loop offers an array of lunch spots, perfect for whatever your heart desires. Avli on the park serves contemporary Greek cuisine right next to Millennium Park. Native Food Cafe is ideal for a quick lunch for vegan/vegetarian travellers. For a restaurant with a view, opt for a Mediterranean restaurant by the water beatnik on the river.
Don’t forget to stop at the largest Starbucks in the world on Michigan Avenue – yes, totally worth it.
Explore a Chicago museum
For lovers of art museums, explore the Museum of Modern Art, Chicago’s innovative and contemporary art collection located near Water Tower Place. For something free, check out Harold Washington Library or Chicago Cultural Center.
Shop till you drop on The Mag Mile
The Magnificent Mile, a 13-block stretch of Michigan Avenue, is Chicago’s premier shopping district. Shopping highlights include Macy’s, Water Tower Place, 900 N. Michigan Shops, The Shops at North Bridge, and Bloomingdales.
Wine and dine yourself at Lil’ Ba-Ba-Reeba, a classic Spanish restaurant serving tapas, paella, pintxos and sangria. The small portions make this the perfect opportunity for a solo diner to try several dishes.
Another wonderful option for a solo date is Brasserie, café and Venteux oyster bar, a chic French bistro, located inside the Pendry Hotel. Take a seat at the bar and enjoy snails, steak frites and more classic dishes.
Meet new friends
When traveling solo, I recommend staying at a hostel. Hostels are a social hub, a great place to meet other travelers and make friends with like-minded people. They often organize events and activities to encourage connections. A great option is the chicago freehand, which offers shared and private rooms. Mingle at their cocktail bar, the Shaker brokenand check out DJ sets and dance parties on their Event calendar.
Day 2: A taste of Chicago’s neighborhoods
Take the ‘L’Chicago Metro, Red Line to Andersonville, a Chicago neighborhood known for its LGBTQ+ community, independent cafes, local shops, varied restaurants, and Swedish history. Andersonville is one of my favorite neighborhoods to explore on your own – you can take your time, walk into all the shops if you want, and really take in the welcoming atmosphere.
Download the Belly app to easily navigate the ‘L.’ Add money or a pass to your card using your phone. Or buy a card at any metro station. I recommend buying the day or weekend pass for unlimited use.
Another option: rent a Divvy Bike, Chicago’s bike-sharing system, and ride the Lakefront Trail from downtown to Andersonville. Download the app for quick and easy Divvy bike rental. Stop along the way for epic photos of the skyline.
To eat lunch
Located next to the Bryn Mawr Red Line stop, grab brunch at Mr. Henry, a small intimate café that is always full to bursting. They have great options for vegans and vegetarians and there are often other solo diners.
Andersonville thrift and vintage shops
Save your souvenir shopping for day two, so you can find unique Chicago shirts or mugs at Andersonville’s vintage and thrift stores. To verify Buffalo Exchange, Village Discount Outletand The brown elephant. All proceeds from The Brown Elephant benefit LGBTQ+ health and help fund Chicago’s LGBTQ+ health center, Howard Brown Health.
Craving something sweet? Treat yourself! Stopped at Larson lost, a French bakery, for a croissant that will melt in your mouth. Or, stop at the local gluten-free bakery, Of flour for a homemade oat cream pie or an appetizing vegan brownie.
Don’t forget to stop Kopi Travelers Cafe, a local cafe for travel lovers. Not only will you find great coffee, but also a range of travel books and jewelery from around the world. It’s a great place to meet other adventure-loving solo travelers.
Lunch + shopping at Asia on Argyle
Take the red line back and walk it back to the Argyle stop in the Downtown district. This area is commonly referred to as “Asia on Argyle”, a street filled with Asian markets, tea houses, gift shops, delicious restaurants and more. I always feel like I’m traveling solo in Vietnam walking through Argyle.
While you’re there, explore the Tai Nam Food Market. Have a spicy mango latte at First SIP cafe or stop for boba tea at Tao tea. Get some banh mi sandwiches at Ba Le or sample traditional Cantonese dishes at honeymoon coffee. Take your time and explore all the Asian markets and gift shops in the neighborhood.
Have dinner at Downtown Pho for a delicious Vietnamese pho or Cafe Hoang for Thai and Vietnamese dishes. Bring a book and dine by the window so you can watch Argyle fill with life in the evening.
After dinner, go to green mill for late night jazz music. The Green Mill is a legendary entertainment venue famous for its jazz performances and storied past – it was a favorite of notorious gangster Al Capone. Sit at the bar and listen to the smooth, sultry melodies of Chicago jazz.
One last cocktail
For a nightcap, have a martini with a new Uptown hostel friend Fat cat, with an extensive craft cocktail menu, an outdoor patio, and plenty of bar games. Cheers for your fun solo weekend in Chicago and come back soon!