Chicago is America’s fourth-biggest city – but it’s possible to see its highlights in one weekend thanks to it being much smaller and easier to navigate than New York City, Los Angeles or San Francisco. In 48 hours, you can squeeze in sights including Millennium Park, the Art Institute and the Skydeck, explore a cool neighbourhood or two, taste the best of Chicago’s culinary offerings and tick off the city’s premier cultural experiences, including musical Hamilton. Let’s go.

Day One


Exploring on foot is the best way to soak up the atmosphere and get acquainted with the city’s layout. Start at DuSable Bridge, which connects the north and south parts of Michigan Avenue over the Chicago River. It’s the perfect spot to admire the view of Chicago’s skyscrapers and yellow water taxis ferrying people across the water. From here, head south on Michigan Avenue towards Millennium Park. On the way is Free Rein, a stylish brunch spot inside the St. Jane Hotel, and the American Writer’s Museum, a newcomer to the Chicago cultural scene that literature lovers will adore for its exhibitions on the country’s most celebrated authors.

Millenium Park

One block down you’ll hit Millennium Park, Chicago’s most beloved green space and home of the Cloud Gate mirrored sculpture, aka The Bean. A three-minute walk south of Cloud Gate is the Art Institute of Chicago, home to more than 300,000 works spanning French Impressionists, Modern American Art, photography, design, textiles, Islamic Art, Medieval and Renaissance exhibitions. Famous works on show include Van Gogh’s The Bedroom, A Sunday On La Grande Jatte by Seurat and O’Keefe’s Sky Above Clouds IV.


Revival Food Hall, a 10-minute walk from the Art Institute, brings together some of Chicago’s best cuisine in an industrial-chic space. Order a hot, salty ramen at Furious Spoon, try Chicago’s famous deep-dish pizza at Union Squared or sample the modern Indian cuisine from the award-winning Chicago restaurant Pub Royale. Refuelled, walk six minutes west along West Adams Street and you’ll arrive at Skydeck Chicago, the observation deck on the 103rd floor of Willis Tower. On a clear day, the 360-degree views stretch up to 80 kilometres away. Thrillseekers can step out onto the transparent ledge for views straight down to the city.


For dinner, ‘restaurant row’ is a stretch of upscale eateries on Randolph Street between Halsted and Ogden Avenue in the West Loop. Girl And The Goat is a Chicago culinary highlight, a modern-American restaurant with global influences in a large, industrial dining room. Seared scallops in maitake and wood ear mushrooms are perfectly balanced; the goat empanadas are crisp bundles of tender, juicy meat. Alternatively, two blocks north on West Fulton is The Publican, a self-described “homage to oysters, pork and beer”. The Publican’s menu offers hearty American dishes made with seasonal, local and sustainable ingredients – and an astonishing number of brews – in a German beer hall-style space dominated by a long communal table.

After dinner, seek out live jazz. Winter’s Jazz Club, two blocks from the river in the North Loop, seats about 100 people at small, candle-lit tables and hosts a wide collection local and international acts. Winter’s is a listening club – talking while the musicians perform is considered rude – so if you’re in the mood for something for spirited, see a show at Second City, the sketch comedy improv club where Tina Fey, Steve Carrell and many other stars got their start. Second City is in Old Town, a historic neighbourhood known for its nightlife, so you’ll have no trouble finding a bar for a nightcap after the performance.

Day Two


Chicago is famous for its Art Deco skyscrapers and all-round impressive architecture. One of the best ways to admire the beautiful buildings is from the water on a Chicago’s First Lady Cruise Architecture Tour, where an official Architecture Foundation guide explains the story behind the Wrigley Building, the Leo Burnett Building and other skyline highlights.

After disembarking at DuSable Bridge, go north on Michigan Avenue and you’ll find yourself on the Magnificent Mile, Chicago’s premier shopping district. It’s dominated by global chains and American department stores, including Bloomingdale’s and Saks Fifth Avenue. If you’re looking for a more authentic Chicago experience, hop in a taxi or Uber and head 15 minutes south to Pilsen. The neighbourhood is known for vintage stores, street murals and authentic Mexican cuisine. Start at 606 Records on West 18th Street and head west; you’ll also pass Shady Rest Vintage & Vinyl, Pilsen Vintage, Very Best Vintage and Mestiza Shop.


Street art is everywhere in Pilsen but make sure to South Ashland Avenue to Jeff Zimmerman’s four-storey murals: three works side-by-side on a residential building which depict stories about Pilsen’s Latino and immigrant communities. From here, it’s a five-minute walk west along West 19th Street to the National Museum of Mexican Art. The oft-overlooked gallery has works by Diego Rivera and Frida Kahlo, as well as many by emerging Mexican artists.

Another must-visit Chicago neighbourhood is Bucktown/Wicker Park, about 20 minutes by car north of Pilsen. The area is a treasure trove of hip bars, cool boutiques and great locally owned businesses. Have lunch at Dove’s Luncheonette, a casual Tex-Mex eatery in a retro diner, then hop over to North Milwaukee to browse Volumes BookCafe, Store B Vintage and Transit Tees, and get a caffeine hit at The Wormhole Coffee, an ‘80s themed café with a full-sized replica DeLorean time machine from Back To The Future.


For sunset drinks, the rooftop bar on the 13-th storey of The Robey boutique offers unobstructed views of the Chicago skyline as the sky turns pink, orange and purple. Afterward, sneak in a cocktail at The Violet Hour, a speakeasy hidden behind an inconspicuous black wall opposite Big Star tacos. Expertly crafted drinks, a fireplace and a ‘mobile phones out of sight’ policy sets a rarefied tone. Order a Juliet & Romeo: Beefeater gin, lime, cucumber, mint and rosewater.

You’ll want to order a bar snack or two as well, since you may not have time for a sit-down dinner. Hamilton: The Musical is playing at Chicago’s CIBC Theatre, and with ticket prices more reasonable than in New York City, it’s easily justified. The award-winning production by Lin-Manuel Miranda goes for two hours and 45 minutes with an intermission.

If you’re peckish after the show (which will finish at around 10.30pm) go for a late dinner at Celeste, a refined restaurant split over three levels where the drinking, dining and general revelry goes until late.

Book now

Find flights

SEE ALSO: Read Before You Leave – Chicago

You may also like