May 2, 2024  •   5 min read


Chicago – The Windy City. This gorgeous city in the Midwest of the USA is known for its magnificent architecture, open green spaces and beaches, and incredibly friendly people.

Situated on the beautiful Lake Michigan, Chicago has been voted the Best Big City in the U.S. seven years in a row! With an amazing food scene, a big river running through the main core, and many walkable avenues, it’s not hard to see why.

Whether you go to in the spring to eat your way through the city, in the summer to experience the fun of the River Walk, or in the autumn to take in the wonders at The Art Institute of Chicago, this city is a stop worth visiting.


W H E R E  T O  S T A Y


A chicer alternative to Airbnb, Sonder is a hotel alternative that aims to inspire and delight, fulfill needs without sacrificing style, and most importantly, deliver seamless, personalized experiences. With accommodations in over 40 cities in 10 countries, Sonder helps you roam like home in an elevated yet relaxed way. Walking distance to all the sites, boutique shops and global cuisine, this minimal accommodation will be the perfect sanctuary after a busy day.

Address: Many locations in the city

Photo courtesy of Sonder


W H E R E  T O  E A T


Mindy’s Bakery

An absolute must while in Chicago, a visit to Mindy’s Bakery is the best way to start the day! With Eastern European, French, Italian and Middle Eastern influences, Mindy’s is a melting pot of goodness, filling your soul up with nourishment, joy and comfort. Owner, Mindy Segal, has been selected as the “Outstanding Pastry Chef” in the country by the James Beard Foundation, and she opened her namesake bakery, Mindy’s, in 2022, where she continues to dedicate herself to her artisanal craft of baked goods and good eats. Go early for the bagels (they sell out fast!), and get the cinnamon rolls and quiche!

Address: 1623 N Milwaukee Avenue

Photos Courtesy of Mindy’s


Levain Bakery

Originally from NYC, this country-wide bakery is becoming a cult favourite. Opened in 1995 by two best friends, Levain is known for their ultimate chocolate chip walnut cookie – an iconic cookie that draws epicurious travellers from around the world. Levain’s unique philosophy is centred around authenticity, kindness and reciprocity, as everything is baked fresh, on-site, every day, with the day’s leftovers being donated to charity each night. Check out their West Loop and River North locations for some delicious baked goods!

Address: 840 W Randolph Street | 408 N Clark Street

Photos Courtesy of Levain Bakery



Part of the Alinea Group, Roister is a 1 Michelin Star restaurant founded in 2016 by Chef Grant Achatz and Nick Kokonas, with many accolades and awards under its belt. Roister’s food is rooted in primal cooking techniques through a modern lens. Roister elevates comforting, rustic dishes with fine dining techniques and global flavours. We went for brunch and it was both wonderfully delicious and curious. 

Addresses: 951 W Fulton Market

Photos courtesy of Roister


Ciccio Mio 

Stepping into Ciccio Mio is like entering a cozy family friend’s living room. With low-lighting, walls crammed with photographs, and a menu of Italian-American comfort food, this restaurant is an absolute must when in Chicago. Pastas are all made in-house (get the Spicy Vodka Rigatoni and Truffle Bucatini) and their desserts are a wonder – the Tiramisu is the largest one I’ve ever seen, and the Fior Di Latte Gelato comes dusted in fennel pollen, drizzled in chestnut honey – worth every bite!

Address: 226 W Kinzie Street

Photos courtesy of Ciccio Mio


The Allis 

Located on the ground floor of Soho House Chicago, The Allis is open to non-members and is a gorgeous place for brunch, high tea, or dinner. The Allis Bar is named after the family that commissioned the restaurant’s historic building in 1907, and this relaxed space offers up an industrial chic vibe, with floor-to-ceiling windows and an expansive art collection. You can expect light Mediterranean fare with a French twist – the perfect place for a girl’s afternoon.

Address: 113-125 N Green Street

Photos courtesy of The Allis


The Gage

Situated just steps from Millennium Park along Chicago’s Cultural Mile, The Gage is an upmarket gastropub with a superb seasonal menu and drinks program. The decor is a blend of relaxed and vintage 1930s industrial, with green subway tiled walls and reclaimed factory glass in the windows. Known for its European-American food, the menu is eclectic and continuously evolving. A good place to refuel after a visit to The Art Institute of Chicago.

Address: 24 S Michigan Avenue

Photos courtesy of The Gage


Other Notable Eateries:

Hero Coffee Bar | Coffee Shop
Sawada Coffee | Vietnamese Coffee
Nomad Coffee | Coffee Shop
Doughnut Vault | Old Fashioned Doughnuts
Venteux | French Bistro 
Pequod’s | Deep Dish Pizza
Maison Marcel | French-American Cafe
3 Arts Cafe | Cafe in Restoration Hardware 
Gilt Bar | Sister Restaurant of Ciccio Mio 
Handlebar | Vegetarian and Vegan


W H E R E  T O  S H O P



While not the most sustainable fashion brand out there (owned by J. Crew), Madewell is committed to doing better for people and planet. Earlier this year they launched their first line of products made with regenerative cotton, and they’ve also created a strategic approach focused on protecting biodiversity. Their trade-in program operates in partnership with thredUP, which has enabled them to resell 1.6 million pre-loved garments. They have three Chicago locations where you can find some beautiful pieces.

Address: 932 N Rush Street | 855 W Randolph Street | 3442 N Southport Avenue

Photos courtesy of Madewell


Other Notable Shops:

Humboldt House | A Feminist Home Goods & Lifestyle Shop
Space 519 | Lifestyle & Clothing Shop
Wilderhouse | Curated Home Goods & Apothecary


W H E R E  T O  V I S I T


Art Institute of Chicago

Founded in 1897, the Art Institute of Chicago is one of the world’s largest museums, housing an extraordinary collection of artworks across places, cultures and time. The building itself is absolutely stunning, and the gallery houses art from some of the most well-known artists in the world – Van Gogh, Monet, Cezanne, Picasso, Chagall, Seurat, alongside modern and contemporary painters as well. Spend the day here (try to go on a weekday to avoid crowds), and bask in the beauty of it all.

Address: 111 S Michigan Avenue


The Bean

Cloud Gate – known as The Bean – is one of the most iconic structures in the city, one of the world’s largest permanent outdoor art installations, and it has become synonymous with Chicago’s built environment. Located in Millennium Park, the surface of The Bean reflects Chicago’s famous skyline and the surrounding green space. Designed by internationally acclaimed artist Anish Kapoor, an Indian-British sculptor, well-known for his large-scale outdoor works, with The Bean being his first American artwork.

Address: 201 E Randolph Street


Other Notable Sites:

The Rookery | One of Chicago’s most well-known buildings
River Walk | Boardwalk along the river


Save this post for later on Pinterest


Pin It on Pinterest

Share This