Travel Guide: Chicago


I lived in Chicago from June to December and got to experience (1) Lollapalooza in Grant Park (2) a Chicago Cubs baseball game in iconic Wrigley Field (3) American Thanksgiving and (4) Christmas Markets during the Holiday season. Chicago is an amazing city with world-class food, nightlife and activities. During the summer, I was obsessed with running Chicago's scenic Lakefront Trail, an 18-mile paved path that follows the Lake Michigan shoreline. I took the "L" train all around the city to see different neighbourhoods—riding on the elevated infrastructure with skyscrapers surrrounding you is a surreal feeling. I rented a boat with friends and cruised the Chicago River and frequented some of the best restaurants and bars including Alinea, the Aviary and Au Cheval (said to be the best burger in America). Don't miss the Chicago Riverwalk, a path that follows the Chicago River and the Magnificent Mile, a central street with notable shops and hotels.

Food & Drink

Top Restaurants
  • Au Cheval Said to be the best burger in America! This open kitchen at this upscale "diner" works with ingredients ranging from bologna to foie gras. The vibe here is also great for grabbing drinks!
  • Roister Restaurant Went here for brunch and was absolutely blown away. The food and ambiance were amazing—I need to go back to try out dinner! Roister’s food is rooted in primal cooking techniques combined with modern technology when it produces better results. The results are a combination of understated platings and vibrant flavors.
  • Girl and The Goat & Little Goat Diner Both of these great restaurants are owned by American chef and television personality, Stephanie Izard. Girl & The Goat is a hot spot that serves innovative small plates from a dramatic open kitchen. Little Goat Diner has a huge menu of creative, gourmet takes on comfort food classics.

Top Bars
  • The Violet Hour The Violet Hour serves artisanal cocktails in the heart of Wicker Park. Rooted in pre-prohibition style libations, the James Beard Award-winning bar program features a seasonally rotating cocktail list, as well as an extensive selection of approachable and sought-after spirits.
  • The Aviary An elevated cocktail experience brought to you by the Alinea Group (founded/owned by one of the most awarded and recognized chefs in the world, Grant Achatz). The Aviary has signature 5-course tasting menus featuring their best-known cocktails paired with delicious bites. It's an experience to visit. But note the hefty price tag of $150 per person for a 5-course cocktail tasting and $30 per person to reserve a table.
  • Boiler room Trendy, retro spot with an outdoor patio offering gourmet pies alongside craft beer & cocktails. Note The PB&J special: any slice, can of PBR & shot of Jameson. The design is a mixture of trendy & trashy using retired CTA train parts.

Pedestrian-Friendly Streets
  • Michigan Avenue & Magnificent Mile The Magnificent Mile encompasses the 13-block stretch of North Michigan Avenue that runs from the Chicago River to Oak Street. With more than 460 stores, 275 restaurants, 60 hotels and unique entertainments and attractions packed and stacked along its length, The Magnificent Mile has an indulgence for every passion and every pocket.
  • North Clark Street in Wrigleyville Close to Wrigley Field, this is the go-to street for before and after Chicago Cubs games. The strip is packed with sports bars and restaurants. On a busy game day there really is no place like it! Go to a Cubs game to complete the activity.
  • North Rush Street North Rush Street (aka the Viagra Triangle) in the Gold Coast neighbourhood of Chicago is a great street. Just north of downtown Chicago, the Gold Coast is one of the wealthiest neighbourhoods in the entire US. Rush St is home to some of Chicago’s most famous bars, restaurants and shops.

Other Food & Drink

Other Food • Nookies Too (best breakfast in the best residential neighbourhood, Lincoln Park), Ada street, Avec, Big Star (chill Mexican), Carriage House

Other Drink • Soho House, John Hancock tower (95th floor), Gilt Bar (& Library speakeasy), Billy Sunday

Coffee Shops • Intelligentsia, Osmium Coffee Bar, Gaslight Coffee Roasters, Metric Coffee Co, Sawada Coffee, Bridgeport Coffee Company

Activities & Attractions

Top Activities
  • Rent a boat on the Chicago River Rent a boat from the Chicago Electric Boat Company. Cruising in an electric boat is a unique, memorable and environmentally friendly way to see the great city of Chicago. Have fun with friends while having drinks in the sun or use the boat to tour the city of Chicago from the water (note: Chicago has a well known river boat architecture tour, so you can do this tour yourself in your boat or book tickets to have a guide tell you about the city of Chicago).
  • Watch a Chicago Cubs baseball game in iconic Wrigley Field Wrigley Field is the oldest National League ballpark and has been home to the Chicago Cubs since 1916. Going to a game is entirely nostalgic and exciting. If you really want to step up your experience book a "Wrigley Rooftop" to watch the game—unlimited food and drink while watching the game from a comfortable and surreal setting. Visit the North Clark Street strip before or after the game for the full experience.
  • Run or walk Chicago's scenic Lakefront Trail This is one of the best waterfront paths out of any city. During the summer months, this path is packed with people doing various activities. When I lived in Chicago, I would run this trail every day!


Sites • The Bean (Cloud Gate) located in Millennium Park

Parks • Millennium Park, Grant Park, Oz Park in Lincoln Park

Other Activities • On the weekend have breakfast at Nookies Too in Lincoln Park, a really great breakfast spot. Afterward walk around Oz Park. Oz Park was named in honour of Lyman Frank Baum (1856-1919), the author of The Wonderful Wizard of Oz. Baum lived in Chicago, several miles west of what is now the park. The neighbourhood of Lincoln Park is beautiful and should be given a slow day to explore.



Wicker Park, River North, The Magnificent Mile & North Rush Street, Lincoln Park, Logan Square, Loop, Lakefront Trail (great for runs) and Wrigleyville

Hotels & Airbnbs
The Peninsula Chicago • The Peninsula Chicago is the five-star hotel that brought traditional Asian service to a city already renowned for the warmth of its hospitality. The hotel has become an integral part of Chicago life and is considered the top choice for everything from accommodation to celebrations and corporate events.
Viceroy Chicago • Seek out our stylish retreat in the Gold Coast, on the site of a 120-year-old landmark building, representing one of the finest hotels near Chicago’s Magnificent Mile
The Drake • No other Chicago hotel has inspired more legendary acclaim on par with The Drake. This timeless property affords guests easy access to the city's most exclusive shopping, nightlife and dining.