Destination Guide
Chicago
Get swept up in the windy city full of culture, fun and food.
Destination Guide Chicago
How I See Chicago
The Windy City. Chi-Town. The Second City. There’s plenty of names for Chicago. I simply call it: HOME. From its sprawling parks to its towering skyscrapers and eclectic neighborhoods, this city is a playground. Whether enjoying a sunrise sprint along Lake Michigan or biking one of its many trails, you'll enjoy amazing views all around. Chicago may be the home of blues music, but nothing here will leave you feeling down.
When In Chicago You Must
EAT
The Delta
1745 W North Ave
DRINK
JoJo's Milk Bar
23 W Hubbard St
SHOP
Fat Tiger Workshop
836 N Milwaukee Ave
PLAY
Headquarters Beercade
213 W Institute Pl
Talk Like A Local
Know the slang of the city
Merch
/mərCH/ verb.
To offer proof.
I saw Dave at the movies with another woman and I have the photos to merch it.
Neighborhoods to explore
Chicago's neighborhoods are each like a character of their own. Get to know all of the best places to explore.
1. Bronzeville
Known as the “Black Metropolis” in the early 20th century, this historic neighborhood is central to Chicago’s storied Blues & Jazz scenes and served as home to some of that period’s greatest African-American actors, actresses, poets, and musicians.
2. Pilsen
This colorful, vibrant, multicultural neighborhood is home to some of the city’s best street art, drenched in the Latinx history of the majority of its residents.
3. Logan Square
This thriving, artsy community is the city’s central hub for everything local, lined with dive bars serving local craft beers, music venues & galleries showcasing local artists, and local restaurants.
4. River North
Party central! You’ll find some of the hottest nightclubs and swankest restaurants the city has to offer in this bustling neighborhood.
Ultimate Access to Chicago
Seasons change but we’ve got you covered on the hottest spots in the city.
Virgil Abloh: "FIGURES OF SPEECH" at MCA Chicago
220 E. Chicago Ave.
MCA Chicago’s latest exhibition explores designer Virgil Abloh's career, including his time as creative director for Kanye West, his popular streetwear company Off-White and the various high-profile collaborations he's had a hand in, along with his recently landed role as the artistic director of Louis Vuitton.
DeJuan Evans / Insider
Don’t skip the exhibit’s exclusive, pop-up gift shop, “Church & State.”
Violet Hour
1520 N. Damen Ave.
It may be hard to locate the doorway, covered by the wall of random and frequently rotating graffiti art, of this hidden retreat, but the cocktails are worth the hunt.
DeJuan Evans / Insider
Always obey the “House Rules.”
The Mousetrap (Off Color Brewing)
1460 N. Kingsbury St.
Off Color Brewing’s flagship taproom, aptly named after the little critter on their logo, not only offers a bar stocked with the brand’s current, full line of craft beers in production for beer lovers, they also host educational tours and tastings in their adjacent brewhouse and serve wine & spirits as well.
DeJuan Evans / Insider
Go for my personal fav, “The One Percent.”
Boneyard
1102 N. Ashland Ave.
One of Chicago’s up-and-coming streetwear consignment hubs specializing in vintage goods, rare fashion pieces, and highly sought after sneakers.
DeJuan Evans / Insider
Be sure to bring cash (and a rabbit’s foot) for your chance to win at their key master machine, loaded with exclusive kicks.
Either / Or
DETOX
Left Coast Food + Juice
717 N Wells St
From their amazing açai bowl to their assortment of delicious smoothies, this spot will provide you with the fuel to push through that 9am meeting or rough morning-after.
RETOX
Prysm Nightclub
1543 N Kingsbury
Gather the gang and party the night away to the sounds of some of the world's most notable DJ's, at one of Chicago's hottest nightclubs.
W Chicago - Lakeshore
Urban energy with lakeside views make the perfect city escape.
W Chicago - City Center
Experience the thriving culture of downtown.
Spotted in Chicago
5 Minutes with Years & Years
Talking travel must-haves with British electronica trio Years & Years after their show at W Chicago - City Center.
Mick Rock Zooms in on Talent
Legendary rock photographer Mick Rock gets up close with Jessie Ware, Janelle Monae, and more at W Hotels.
Artpentry
1827 South Halsted St
Artpentry is an independent wood shop and gallery space selling The Gentleman’s Boombox, an object d’art that will remix the way you play music.
Millenium Park
201 E. Randolph St
Located next to the Art Institute of Chicago, this 25-acre, art-filled park is a Chicago must-see.
IKRAM
15 East Huron St
This celebrated boutique has couture pieces and cult brands rare to even more renowned shopping destinations like New York and L.A.
Peter Field
330 S. Wells St
Take a look around at the fine tailored menswear or delve into the leather accessories and bowties.
Brooklyn Boulders
100 South Morgan St
Get out of your comfort zone with a whopping 23,000 square feet of climbing terrain located just minutes away in the West Loop.
CURRENT
W Chicago – Lakeshore
A fresh, modern take on seasonal Italian cuisine showcasing simple and soulful dishes alongside hand-crafted Italian cocktails, a boutique wine list, wines on tap, and an array of local microbrews.
Reggies Live
2105 South State St
One part rock club, one part restaurant and another part old school record store.
The Mid
306 N Halsted St
Headliners such A-Track, The Magician, Tiesto and more won’t pass through Chicago without a stop at The Mid.