Chicago is a testament to the rich history that has long graced the American Midwest, on display through iconic landmarks, diverse neighborhoods, and a resilience that continues to shape its vibrant art and design identity. Here’s what to do this weekend to experience the best of Chicago.
Known as an architectural titan in the American design sphere, Chicago’s evolution from a small trading post in the 18th century to a bustling metropolis continues to delight, drawing over thirty million visitors each year. Founded in 1833, the city’s idyllic spot on the coast of Lake Michigan facilitated its growth as a transportation hub and a center for industry and commerce. As a city that has had to rebuild again and again throughout its lifetime, its grand architectural designs and intuitive urban planning are a sight to behold. Let’s take a deep dive into how to explore Chicago’s rich culture and how its history permeates into its must-see stops today.
How to prep for a trip to Chicago
Chicago is designed to be a walkable metropolis with plenty of sights to take in, seen with a quick glance at its impressive skyline. Much like New York, Chicago was built on a grid system with the intersection of State and Madison Streets as the midpoint of the grid. This means you’ll be able to easily find your way around the city and back to a home base when tracing what to do this weekend in Chicago.
The city is also home to a plethora of seasonal activities and festivals. The Chicago Blues Festival (June 2024), the Taste of Chicago (June 24 at Humboldt Park, July 15 at Pullman Park, August 5 at Marquette Park), and Lollapalooza (August 3-6) bring famed musicians and chefs north for summer; on the other hand, winter ushers in the Christkindlmarket wonderland. While springtime and summer in Chicago offer temperate climates filled with blossoming tulips and sunshine on Lake Michigan, The Windy City becomes truly, well, windy during the autumn and winter. Therefore, we recommend packing plenty of urban chic layers so that you’re prepared for whatever Chicago’s weather throws your way.
Where to stay in Chicago
Between the impressive private art collection and award-winning cuisine it houses, Park Hyatt Chicago exudes contemporary chic. This legendary property is the ideal home base for anyone looking for immediate access to the city’s most exciting attractions and exemplary service. In addition to being located next to the iconic Magnificent Mile, the hotel is also home to delicious dining options and premiere wellness facilities – all adding to the growing list of what to do this weekend in Chicago.
Park Hyatt Chicago offers 198 rooms – including thirteen elegant suites – each appointed with deep soaking tubs and sleek window benches with views of the Water Tower, Lake Michigan, and Chicago’s Gold Coast. Suites offer apartment-style layouts with separate living areas, as well as a range of residential features such as a kitchenette and powder room that make guests feel right at home in downtown Chicago. These elegantly understated rooms ensure a plush, comfortable stay.
The dining options at Park Hyatt Chicago are a particular highlight for a weekend outing. Their main dining area, NoMI, is named for its iconic location on North Michigan Avenue. NoMi’s team treats guests to an array of French-inspired American cuisine by Executive Chef Terence Zubieta. NoMI Lounge offers a more relaxed experience and Chicago’s best sushi alongside craft cocktails from an extensive global collection. The lounge also invites guests inside their working wine cellar that houses a specially curated global wine collection. Uncorking and sipping on the rare and unique curated wines is a particularly satisfying experience here with all wines vetted by sommelier Jillian Riley Looking for an open-air experience? Check out the NoMI Garden outdoor terrace and dine under in the midst of Chicago’s skyline.
Where to find the best Chicago architecture
In good company woven into the American architectural tapestry with the likes of New York’s Chrysler Building and Seattle’s Space Needle, Chicago is renowned for its distinct palette of hypermodern and old-world buildings. From River North to Logan Square, there is an impressive array of eye-catching facades harking back to a span of time periods along the historical spectrum. This wide array of architecture is all thanks to the city’s central location in key trade routes during the 19th century, as well as its ability to rebuild after the Great Chicago Fire of 1871 which leveled nearly 17,500 buildings.
There are a couple of ways to explore this city’s architectural marvels: one popular option for what to do this weekend in Chicago is to hop onto a boat tour along the famed Chicago River. With departures around the clock, rain or shine, your knowledgeable guide will take you through an incredible breadth of history that outlines how the city rose from the ashes to build bigger and better. Our personal favorite way of exploring Chicago’s architecture scene is via a private guided walking tour, all arrangeable via your SmartFlyer travel advisor.
An overview of the Chicago shopping scene
Chicago offers a range of shopping experiences, from the Magnificent Mile’s upscale boutiques, flagship stores, and luxury brands to Wicker Park’s independent boutiques and local artisans. Though, a lesser-known hidden gem amongst the city’s glamorous retail scene is its secondhand shopping scene. Thanks to the Windy City’s eclectic and vibrant history with design, you can find some truly rare finds in flea markets and vintage stores.
Our top neighborhoods for Chicago shopping
- Andersonville: When it comes to shopping from locally-sourced shops, there’s no better place to start than in Andersonville. Located on the north side of Chicago, this vibrant neighborhood is known for Chicago-only vendors such as the Andersonville Galleria and Milk Handemade, featuring quirky home decor and artisanal crafts. Strolling along Clark Street is a treat in itself: just window shopping is sure to give you a taste of Chicago’s ever-burgeoning art scene bleeding into its fashion.
- Hyde Park: There’s a reason why this is one of the most well-known cultural hubs in the States. With the esteemed University of Chicago nearby, Hyde Park is a must-visit to unlock your inner scholar. Its maze of boulevards contains 57th Street Books, a labyrinth of books containing deep backlists of rare finds collected and curated by their enthusiastic staff. The Silver Room – an institution founded on the mission to curate a shopping experience that reflects Chicago’s global community – also offers one-of-a-kind apparel, apothecary, accessories, books, and gifts.
- Pilsen: This neighborhood is known for its vibrant Mexican heritage and is lined with trendy bars, family-owned taquerias, and distinctly Latin American shopping. There are a variety of vintage shops clustered near the area’s main stretch on 18th Street such as Pilsen Vintage and Knee Deep Vintage. If you’re looking to bring home a piece of Mexican-American artistry, Mestiza is the place to go. Two Latine entrepreneurs founded this colorful boutique was founded by to support socially conscious shopping and local artists.
- Wicker Park: Chicago’s art community thrives here with its indie shopping, vintage stores, record shops, and more. Exciting storefronts that blend edgy design with cozy Brooklyn coffee shop vibes dot the intersection of Milwaukee, Damen, and North Avenues. One particular highlight is Shuga Records, an indie music label and record store that offers a wide range of vinyl tagged with recommendations from its friendly staff. Asrai Garden and Una Mae are our go-to’s for unique contemporary clothing labels and curiosities.
Best theatre in Chicago
Looking to find a unique evening outing for what to do this weekend in Chicago? While many will cite New York City for the Great White Way and its vibrant Off- and Off-Off-Broadway community, Chicago is where thespians flock to in order to discover new, cutting-edge productions yet to grace Broadway. Comedy fans also regard the city for its rich improv scene that helped in the meteoric rise of iconic performers like Amy Poehler and Stephen Colbert.
SmartFlyer picks for a night at the theatre
- Chicago Shakespeare: Located on Navy Pier, this theatre focuses on reimagining classics such as Twelfth Night and Midsummer Night’s Dream for a contemporary audience. The theatre is also integral in the development of new projects from musicals to plays.
- Goodman Theatre: This professional theatre company has been the developmental grounds for many iconic musicals and plays. An example of their pulse on the cultural zeitgeist favoring 90s remakes is a recent production of The Who’s Tommy, an iconic rock opera whose last large-scale production hit Broadway in 1993.
- Hell in a Handbag: Susan Sontag defines “Camp” as “an intentional over-the-top-ness, a slightly (or extremely) ‘off’ quality, bad taste as a vehicle for good art.” This theatre company’s eclectic mix of comedic productions mounted around the year embodies each part of that definition and are an ideal way to kick off your Chicago weekend.
- Lifeline Theatre: Lifeline Theatre reimagines books and other literary works and adapts them for the stage. Past productions include world premieres of Treasure Island, Wuthering Heights, and Frankenstein.
- Lookingglass Theatre: Founded in 1988 by graduates of Northwestern University, Lookingglass Theatre Company is a nonprofit theatre that focuses on the development of new works staged at the emblematic Water Tower. The theatre also provides theatre education to Chicago-area students and teachers through various Education and Community Programs.
- Steppenwolf Theatre: Every production that goes up at Steppenwolf guarantees performances that are both visceral and moving. Many thespians quote this ensemble as one of the leaders in physical storytelling.
Ready to take on the Windy City by storm? Contact your SmartFlyer travel advisor today to get planning.
