5 WS: The Best Things to Do When Traveling Alone in Chicago

Traveling alone to big cities can be an exhilarating experience, and Chicago is no exception. Whether you’re a solo traveler or in the city for business, there are plenty of exciting things to do and see. In this article, we will provide you with a weekend itinerary that combines classic Chicago sightseeing with the charm of its neighborhoods.

Day 1: Downtown Chicago + Sightseeing

On your first day of solo travel, immerse yourself in Chicago’s iconic architecture and the magic of the downtown Loop.


Start your day with a delightful breakfast at Stan’s Donuts, known for its scrumptious specialty donuts. Alternatively, you can try Goddess and Baker for a quick breakfast sandwich and coffee.

See the Sights

A fun way to explore downtown and potentially meet other solo travelers is by joining a free walking tour. Free Tours by Foot offers various options, including a Loop/Millennium Park Tour and a Chicago Riverwalk tour. If you prefer to explore on your own, make sure to visit the must-see attractions such as Millennium Park, Cloud Gate (“The Bean”), 875 N. Michigan, Wrigley Building, TheMART, and Chicago Riverwalk.

Solo travel tip: Bring headphones, a book, or a journal for company during your meals. Don’t hesitate to strike up conversations with people around you. Additionally, make sure to bring a tripod to capture memorable photos of yourself and the stunning sights. Downloading a few episodes of your favorite podcast is also a great way to enjoy sightseeing and shopping.

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Chicago’s downtown Loop offers a wide range of lunch spots to satisfy any craving. Avli on the Park serves contemporary Greek cuisine right next to Millennium Park. For vegan/vegetarian travelers, Native Foods Cafe is an excellent choice. If you’re looking for a restaurant with a view, opt for Beatnik on the River, a Mediterranean restaurant located by the waterfront.

Don’t forget to make a stop at the world’s largest Starbucks on Michigan Avenue – it’s an experience worth having.

Explore a Chicago Museum

Art lovers should visit the Museum of Contemporary Art, which houses an impressive collection of innovative and contemporary art. If you prefer something free, check out the Harold Washington Library or the Chicago Cultural Center.

Shop ’til You Drop on The Mag Mile

The Magnificent Mile, a 13-block stretch on Michigan Avenue, is Chicago’s premier shopping district. Macy’s, Water Tower Place, 900 N. Michigan Shops, The Shops at North Bridge, and Bloomingdales are just a few of the famous shopping destinations in the area.


Treat yourself to a delightful dinner experience at Lil’ Ba-Ba-Reeba, a classic Spanish restaurant known for its tapas, paella, pintxos, and sangria. The small portions make it the perfect opportunity for a solo diner to try multiple items. Another fantastic option is Venteux Brasserie, Cafe & Oyster Bar, a chic French bistro located inside the Pendry Hotel. Grab a seat at the bar and indulge in escargot, steak frites, and other classic dishes.

Meet New Friends

For solo travelers looking to meet fellow adventurers, we recommend staying at a hostel. Hostels serve as social hubs and are great places to connect with like-minded people. One recommended option is the Freehand Chicago, which offers both shared and private rooms. Make sure to mingle at their cocktail bar, the Broken Shaker, and check out the DJ sets and dance parties on their events calendar.

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Day 2: A Taste of Chicago’s Neighborhoods

Take advantage of Chicago’s metro system, the ‘L,’ and hop on the Red Line to Andersonville, a vibrant neighborhood known for its LGBTQ+ community, independent coffee shops, locally-owned boutiques, diverse restaurants, and Swedish history. Andersonville is a perfect neighborhood to explore alone, allowing you to take your time and enjoy the welcoming atmosphere.


Start your day off right with brunch at M. Henry, an intimate breakfast café located off the Bryn Mawr Red Line stop. They offer great options for vegans, vegetarians, and you’ll often find other solo diners here.

Andersonville Thrift and Vintage Shops

Save your souvenir shopping for day two and explore the charming vintage and thrift stores in Andersonville. Buffalo Exchange, Village Discount Outlet, and The Brown Elephant are excellent places to find unique Chicago shirts or mugs. It’s worth noting that all proceeds from The Brown Elephant benefit LGBTQ+ health and help fund Chicago’s LGBTQ+ health center, Howard Brown Health.

Neighborhood Treats

Indulge your sweet tooth at Lost Larson, a French bakery known for its mouthwatering croissants. Alternatively, visit Defloured, a gluten-free local bakery, for a homemade oatmeal creme pie or a delicious vegan brownie. For coffee lovers, don’t miss Kopi’s Travelers Cafe, a locally-owned coffee shop that not only serves excellent coffee but also offers an array of travel books and jewelry from around the world. It’s the perfect spot to connect with other adventure-loving solo travelers.

Lunch + Shopping at Asia on Argyle

Head back to the Red Line and make your way to the Uptown neighborhood, specifically the Argyle stop, known as “Asia on Argyle.” This street is filled with Asian markets, tea shops, gift shops, and numerous delicious restaurants. While exploring this vibrant neighborhood, stop by the Tai Nam Food Market, First Sip Cafe for a spicy mango latte, or Tao Tea for boba tea. You can also pick up banh mi sandwiches at Ba Le or enjoy traditional Cantonese dishes at Honeymoon Cafe. Take your time and explore every Asian market and gift shop in the area.

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For dinner, treat yourself to delicious Vietnamese pho at Uptown Pho or savor Thai and Vietnamese fare at Cafe Hoang. Enjoy your meal by the window and witness Argyle come alive in the evening.

Chicago-Style Jazz

After dinner, make your way to the Green Mill for some 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, relax, and let the sweet, sultry melodies of Chicago jazz captivate you.

One Last Cocktail

End your night with a fantastic martini at Fat Cat, an Uptown staple known for its extensive craft cocktail menu, outdoor patio, and bar games. It’s the perfect place to raise a glass to an unforgettable solo weekend in Chicago.

For more information on various topics, please visit 5 WS.

Remember, whether you’re exploring downtown Chicago or discovering its vibrant neighborhoods, traveling alone can be a fulfilling adventure. Embrace the freedom and make lifelong memories in the Windy City.

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