Chicago GUIDE
The Art Institute of Chicago is always a must-visit for me - any chance to see Degas’ Little Dancer! Nearby, the (free) Chicago Cultural Center is home to an incredible Tiffany dome ceiling that’s definitely worth a stop.
When the weather’s nice, an architectural river cruise is a wonderful way to get to know the city - plan this for the beginning of your trip if you can!
No trip to Chicago is complete without shopping at P.O.S.H. - it’s a wonderful mix of vintage and new items, curated by the shop’s charming owner, Karl. He travels to Paris to source vintage finds, and I’m always leaving extra space in my luggage to bring them home. Did I mention there’s a little champagne bar just a couple of doors down?
If you’re visiting with a car in the spring or summer, Chicago’s Botanic Garden is a lovely stop just outside the city. During the holiday season, shop the Christkindlmarket - and catch the Joffrey Ballet’s classic production of The Nutcracker (it’s the absolute best in my book).
Breakfast & Brunch:
Blue Door Kitchen & Garden and The Allis at Soho House (they also do afternoon tea!) are my top picks. The local chain Yolk has a special place in my heart, and I’ll stop into any Dollop Coffee Co. when in need of a cappuccino. The Hampton Social is also a fun brunch spot - equal parts Instagram opportunity and good food.
Lunch & Dinner:
For something casual, head to Velvet Taco or have Chicago’s famous deep-dish pizza (my picks are Giordano’s or Gino’s). For a lingering sit-down meal, try the no-fail RL restaurant, Au Cheval (the burger!!), Margeaux Brasserie, or Maple & Ash. On my list for the future: 3 Arts Club Café, Ēma, Nonnina, and Bavette’s.
Drinks with a View:
The Signature Lounge at the 96th floor of the Hancock building is my all-time favorite - it’s more than worth the wait for a table by the window! The next best view is at London House’s rooftop bar - though Drumbar and Cindy’s are also great spots for a drink with a city view.
Sweets:
If you only get one sweet in Chicago, let it be from Doughnut Vault - quite possibly the best doughnuts ever. For something more Parisian, head to La Fournette, Toni Patisserie, or Alliance Bakery. Ooh, and the delicious Vosges Chocolates!
FOR THE OUTDOOR ENTHUSIAST:
Walk and bike the Lakefront Trail
Kick off your outdoor journey on the Veloway, the perfect bike path for cyclists and rollerbladers. Just a stone's throw away, the Barton Creek Greenbelt beckons with extensive trails ideal for hiking and mountain biking, where you can uncover secluded spots like Sculpture Falls and the Hill of Life. For a refreshing swim, dive into the crystal-clear waters of Barton Springs Pool, available all year round.
Chicago’s iconic Lakefront Trail, which stretches 18.5 miles along Lake Michigan, is lined with beautiful parks, boat harbors, and sandy beaches. It also offers easy access to a variety of top cultural institutions, like Lincoln Park Zoo, Peggy Notebaert Nature Museum, and the South Shore Cultural Center. Plus, the trail is dotted with a variety of scenic waterfront dining options.
Join a guided tour with Bobby’s Bike Hike, which explores lakefront neighborhoods and beaches adjoining the Lakefront Trail. Or grab a Divvy bike as part of the city’s bikeshare program from one of the many Divvy stations across the city, and explore the lakefront at your own speed.
Get your fitness fix on The 606, an elevated biking, walking, running, rollerblading, and skateboarding-friendly path on Chicago’s northwest side.
The unique path transformed an abandoned railway line into one of the city’s most popular and beautiful outdoor attractions. The paved trail, which rises around 18 feet above street level, is lined with lush greenery, public art, observation areas, and intimate parks.
The trail extends 2.7 miles through four of Chicago’s hippest neighborhoods: Wicker Park, Bucktown, Logan Square, and Humboldt Park. The path is popular with walkers, runners, bikers, and families. You can rent your own set of wheels from a nearby Divvy bike share station or explore the trail on foot.
FOR THE MUSIC LOVER:
Chicago is a premier, year-round live music destination featuring iconic blues clubs like Kingston Mines and Buddy Guy's Legends, legendary rock venues such as Metro and The Riviera, and massive summer festivals like Lollapalooza (Aug 2026) and the free Chicago Blues Festival (June 2026). The city offers diverse genres, from jazz at the Green Mill to indie at The Empty Bottle.
