With its myriad museums, gorgeous green spaces and remarkable restaurants, Chicago is anything but dull. But with so much to do, navigating the Windy City can be daunting.
Luckily, Les Clefs d’Or member and native Chicagoan Philippe Gills is here to help. Having served as Forbes Travel Guide Five-Star The Langham, Chicago’s chef concierge for six years — he was even part of the property’s pre-opening team — the knowledgeable local has learned some helpful tips for traversing the vibrant city.
Follow along as he guides us through this bustling Midwestern metropolis.
What’s the best way to see Chicago in one day?
As an avid runner and Chicago Marathon finisher, I relish the chance to run outdoors, especially during warmer months. Our lakefront trail stretches 18.5 miles and has running/walking and bike lanes along the entire route. In addition to stunning lake and city views, you’ll enjoy the diversity of vibrant neighborhoods — from Lincoln Park on the north to Hyde Park on the south.
Set aside time for an architectural river tour of Chicago. There is no better way to see our architecture. The Chicago River is much narrower than New York’s Hudson River and allows you to get an uninterrupted, up-close perspective. The absence of vehicular and pedestrian traffic allows you to focus on the docents’ interesting historical perspectives as you appreciate the variety of architecture.
Boat and kayak tours on Lake Michigan provide an option to view the entirety of the city from a distance. Private tours require advance planning and are ideal for true historians.
Chicago Greeter lets you experience the city like a local. Select a neighborhood or point of interest, and Chicago Greeter will pair you with an expert who will take you on a two- to four-hour guided experience. One-hour tours are available on Friday, Saturday and Sunday, no reservations required.
Observation decks are a unique way to see the city. Willis Tower, in the financial district, offers amazing views from its 103rd-floor observatory, complete with glass-bottomed cube floors to lure the adventurous.
The John Hancock Building’s 360 Chicago observation deck offers breathtaking city and Lake Michigan views from the 94th floor. 360 is home to TILT. Chicago’s highest thrill ride — an enclosed moving platform — tilts you out over Michigan Avenue, home to premier shopping and Oak Street Beach.
What’s new in town?
Neighborhoods — the way they shift and find new ways to engage locals and visitors. Culturally significant Hyde Park continues to expand with new dining, cultural and entertainment options. This is a point of pride, since I spent part of my childhood there.
The West Loop/Warehouse District is a true dining destination, while Wicker Park and Bucktown continue to deserve the “hip” title. The Chicago Riverwalk continues to be developed and becomes more and more of a destination each year.
The Architectural Foundation recently moved into a gleaming new address designed by [midcentury modern architect Ludwig] Mies van der Rohe. Expanded programming includes a skyscraper gallery with super-size scale models of world-renowned skyscrapers. A rotating roster of models from the best architectural firms in the world are on display. I was stunned by the exhibit and highly recommend it.
Chicago is home to some phenomenal museums. Are there any underrated galleries we should make time for?
Museum of Contemporary Photography. It’s easy to walk by the humble entrance of this small museum located at Columbia College. Step inside, however, and you are treated to globe-spanning work by some of the world’s most creative photographers.
Ed Paschke Art Center. This small museum is actually a gallery dedicated to one of Chicago’s more influential artists: Polish-born Chicagoan Ed Paschke. It also features works of budding local artists.
The Oriental Institute. Located on the University of Chicago Campus, this museum houses a jaw-dropping collection of art and artifacts from ancient Persia, Mesopotamia, Syria and more.
Rebuild Foundation – Stony Island Arts Bank. From artistic visionary Theaster Gates is a platform for art, cultural development and neighborhood transformation. Some of the world’s best-known writers, musical and performing artists visit this rare gem, located a short drive from downtown on South Stony Island Avenue.
The ceiling mural in the Palmer House’s lobby is stunning. This artistic feat is the size of a basketball court and was shipped to Chicago from France in the late 1800s. A nice complement to the mural is the Tiffany Dome inside Chicago Cultural Center.
Yoko Ono has an easy-to-miss permanent sculpture hidden behind the Museum of Science and Industry in Jackson Park called Skylanding. You can’t help but take pictures of its gleaming lotus petals, approximately 12 feet tall. It’s her first permanent sculpture in America.
Where should we book a table for a post-museum meal?
I love what chef[s] John B. Shields [and Karen Urie Shields are] doing with [duel-concept restaurant] Smyth + The Loyalist — divine seasonal cuisine in multicourse — Smyth — and à la carte — The Loyalist — formats in a remarkably warm environment.
Chef Andrew Zimmerman’s Proxi is exciting right now, pushing out a whimsical small-plate menu that celebrates a global street-food concept that is relaxed and exciting at the same time.
Brindille oozes French sophistication, thanks to co-owner and chef Carrie Nahabedian. It boasts one of the more interesting wine programs in Chicago, created by wine director and co-owner Michael Nahabedian.
What about after-dinner drinks?
Milk Room, located in the Chicago Athletic Association, features vintage rums and spirits for bespoke cocktails, courtesy of beverage director Paul McGee and [longtime bartender] Steven Andrews.
Arbella [for its] global-inspired cocktail program, lounge feel and Chicago house beats some evenings, courtesy of local icon DJ Lady D and others.
Call me partial, but I must say Travelle Bar located inside The Langham [is another winner]. This sexy bar offers stunning river views and low-slung Mies-inspired furniture. The atmosphere captures the ’60s-lounge experience, but the real reason to visit is master mixologist James Urycki. This rising star is outstanding and wildly creative. Put simply, if I didn’t work here, I would happily imbibe, just to see what he dreams up next.
If you could give us one piece of advice for visiting Chicago, what would it be?
Don’t sit in traffic, if you’re fine taking public transit, and have minimal luggage. Trains to and from O’Hare and Midway airports are ideal ways to sneak into the city if you arrive during rush hour. Both rail systems make multiple stops within or near major hotels and attractions. Orange Line from Midway, Blue Line from O’Hare, respectively.