Rebecca Mottram Travel Agent

Nicknamed America’s “Second City”, Chicago is making a serious effort to be the USA’s multi-attraction and inclusive short-break destination. I will detail some of the top things to do for a short stay in Chicago so if this is somewhere you know nothing about, or even if you’re ready to get booked, I’d be happy to help you plan.

DAY ONE

MORNING

Take a stroll or jog along the 18-mile Lakefront Trail that skirts Lake Michigan. It connects many of the city’s lakefront parks, beaches, museums, neighbourhoods and restaurants, with skyline views, beaches and beachfront bars.

In summer, enjoy a swim, play beach volleyball, or just sit back on the miles-from-the-ocean sandy beach.

North Avenue Beach is one of Chicago’s most popular beaches with locals and visitors alike, due to its spacious sands, lively bars, and location convenient for other top attractions (like the nearby Lincoln Park Zoo). In the summer, expect firework displays, live music and theatre.

A striking building on North Avenue Beach is the sleek ocean liner-inspired beach house. The top deck is home to Castaways, a casual bar and grill with some stunning views of the city.

Also right on the beach, Shore Club offers a more upscale experience. Sip cocktails with your toes in the sand or reserve a private cabana with personalised bottle service.

Its proximity to downtown and The Magnificent Mile, one of the world’s most iconic shopping districts, makes Oak Street Beach an easy (and scenic) pit stop. From here you also get an up-close view of some classic and timeless Chicago buildings, like 875 N. Michigan Avenue (John Hancock Center) and the historic The Drake Hotel.

On the beach, you’ll find bike rentals, chair rentals and volleyball courts. Oak Street beach hosts popular amateur and professional volleyball tournaments throughout the summer.

Reserve a cabana at Whispers at Oak Street Beach, where you can enjoy waterfront views and upscale beach fare, like ahi tuna nachos, crab cakes, and duck confit tacos.

AFTERNOON

Ride a soaring Ferris wheel, sample classic Chicago eats, hop on a boat tour, and more, at lakefront Navy Pier, one of the Midwest’s most popular attractions. 

Here, FlyOver Chicago is an “immersive journey” that simulates a “flight” over city buildings and landmarks.

Head back into the heart of the city and stroll the downtown streets, taking in the bold and distinctive architecture and skyscrapers such as Willis Tower (formerly the Sears Tower) and the neo-Gothic Tribune Tower. Note the Art Deco buildings dating from the 1920s, which have since come to represent the opulence and glamour of the Roaring Twenties. 

Take a selfie at Cloud Gate, otherwise known as “The Bean”, an oversized kidney-shaped elliptical sculpture near Millennium Park. The monumental work of art, made entirely of stainless steel, reflects the city’s famous skyline. 

EVENING 

Chicago is arguably the home of authentic American pizza – which usually comes with one of three bases: deep-dish, stuffed and Chicago thin. Walk the downtown area and you won’t go more than a few hundred yards without seeing a pizza restaurant. A true Chicago institution is Lou Malnati’s on North Lincoln Avenue, where there are often queues of locals and visitors waiting to get in to taste its deep-dish variety.

An alternative is Thalia Hall,  a landmark concert venue in Chicago’s Pilsen neighbourhood. Designed after the Prague Opera House, Thalia Hall first opened in 1892 as an arts and entertainment space for the community.

Today, the concert hall hosts shows by well-known musical acts, up-and-coming local names, touring comedians, and more. The venue also houses a retro cocktail lounge, a piano bar, and a modern Mexican seafood restaurant.

Then for a spectacular view of the city’s twinkling night lights, head to the 360 CHICAGO observation deck in the John Hancock Observatory, which is open until 23.00. 

DAY TWO

MORNING

Stroll the lively Chicago Riverwalk, home to outdoor cafes, wineries, and shops. The riverwalk comes alive when it is filled with walkers and diners particularly in Summer.

City Cruises offers a variety of architecture tours, including elegant brunch cruises on a glass-enclosed river boat. On a Chicago Architecture Center River Cruise onboard First Lady, hear about the fascinating stories behind more than 50 buildings located along the waterway.

To get your heart pumping, try kayaking  on either the Chicago River or Lake Michigan. You can join a guided tour or rent a kayak to paddle at your own pace — both offer memorable skyline views.

Or see the same via the Chicago Water Taxi, probably the most relaxing way to get around the city.

Enjoy “landscape art under glass” at the historic Garfield Park Conservatory, one of the largest conservatories in the country.

AFTERNOON

Visit the Art Institute of Chicago, which has one of the largest collections of Impressionist art outside the Louvre in Paris, and its stunning Modern art wing. Then go deeper into the Chicago story by learning about the Great Chicago Fire (1871), the Jazz Age (1923-1940) and more at the Chicago History Museum.

Explore Chicago’s diverse character by venturing into its unique neighbourhoods, each offering a distinct atmosphere, culture and an array of attractions beyond the downtown core.

For example, Hyde Park is an academic-minded and culturally rich neighbourhood on the South Side that is home to the University of Chicago and President Barack Obama’s former residence. 

You can tour the Frank Lloyd Wright Frederick C. Robie House, a masterpiece of Prairie Style architecture built in 1909-1910. 

Also in Hyde Park, Osaka Garden is an authentic Japanese garden, gifted to the city during the 1893 World’s Fair, with waterfalls, footbridges, ponds and cherry blossom trees. 

A walk through the Osaka Garden lands you right on the doorstep of the Museum of Science and Industry. The largest science centre in the Western Hemisphere, the museum is full of creative, interactive exhibits about trains, ships, space and even storms.

EVENING

Whether it’s rock, hip hop, punk, blues or jazz, live music pumps out from an extraordinary number of venues on every night of the week. 

Hear Chicago-style blues at Buddy Guy’s Legends in the South Loop neighborhood, owned by the iconic blues guitarist. This famed nightclub keeps the Chicago-style blues tradition alive with nightly shows by local, national and international acts. 

Billed as Chicago’s largest and oldest continuously operating blues club, Kingston Mines in the Lincoln Park neighbourhood has been singing the blues for more than 50 years, while the Empty Bottle, an unassuming storefront on busy Western Avenue in West Town, is one of the city’s premier indie rock clubs. It is known for affordable shows showcasing local and lesser-known acts.

Or for an evening of impressive musical improvisation, visit Howl of the Moon on W. Hubbard Street to see talented musicians take turns in playing a variety of instruments as they take requests from members of the audience – who show their appreciation by throwing dollar bills of various denominations onto the stage.

If this makes you want to head to Chicago, then get in touch as I’d be happy to plan you an amazing trip!