Chicago isn’t a city that shouts. It has a quiet confidence. It’s that classic cool that can’t be replicated. It exudes IYKYK energy.
World-class architecture quietly towers. Michelin-starred eateries share walls with unassuming mom-and-pop shops. Chicago has layers, and the true essence of the city can’t quite be put into words.
We’ve compiled a list of some of our favourite Chicago spots for you to enjoy between #NIRI2026 events. We hope you enjoy seeing Chicago through our eyes.
Welcome to Chicago. A city for those who know, and for those about to know.
THE DAILY GRIND
That first coffee in the morning sets the tone for the day. Here’s where to get your caffeine fix.
Sawada Coffee
112 N Green St, Chicago, IL 60607
A creative playground for coffee lovers, Sawada offers inventive drinks in a gritty, art-filled space. Global barista credentials make every sip memorable and every visit distinctive.
Metric
2021 W Fulton St, Chicago, IL 60612
Metric is a micro-roastery with a minimalist edge. Coffee lovers flock here for the knowledgeable staff and the genuine passion behind every cup.
The Wormhole Coffee
1462 N Milwaukee Ave, Chicago, IL 60622
A quirky neighborhood favorite known for its cozy atmosphere and excellent brews. You may want to spend all day at The Wormhole.
Mojo Coffee
Multiple locations
Mojo brings New Zealand–style coffee culture to downtown Chicago. Blending smooth flat whites and house-made pastries in a modern, sun-drenched café.
Muse Coffee Studio
747 S Western Ave, Chicago, IL 60612
Artistry and warmth is infused in every cup of coffee at Muse. With thoughtfully curated drinks and stylish, light-filled interiors, it’s the perfect place to unwind, work, or simply savor a carefully crafted latte.
BEYOND DEEP DISH
Don’t get us wrong, deep dish is delicious. And we highly recommend you get some (hard to go wrong with an institution like Pequod’s Pizza). But if you’re looking for a culinary adventure, we’ve got you.
Kasama
$$$$
1001 N Winchester Ave, Chicago, IL 60622
Boasting two Michelin stars, Kasama is a husband-and-wife team serving a modern interpretation of Filipino cuisine.
Demera
$
4801 N Broadway, Chicago, IL 60640
If you find yourself Uptown, expect comforting, spicy stews, colourful veggie combos, and a warm, approachable atmosphere. Whether you’ve never had Ethiopian food or it’s a favorite cuisine of yours, Demera will make you feel at home.
Topolobampo
$$$$
445 N Clark St, Chicago, IL 60654
Although deeply rooted in Mexico, Topolobampo reimagines this beloved cuisine in a modern way. And it’s earned Chef Rick Bayless a Michelin star.
Bronzeville Winery
$$
4420 S Cottage Grove Ave, Chicago, IL
Art-filled, music-forward, and decked out with mid-century furnishings, this menu highlights the seasons, with global spins on American classics, and is celebrated for its thoughtful wine list.
Obelix
$$$
700 N Sedgwick St, Chicago, IL 60654
A taste of Paris in the windy city. Incredibly chic, but not stuffy. Classic French techniques meet funky, market-driven plates.
IT’S 5 O’CLOCK SOMEWHERE
Let’s raise a glass to Chicago’s bar scene. Speakeasies, cocktail dives, and sleek lounges where every drink tells a story.
Meadowlark
2812 W Palmer St, Chicago, IL 60647
Tucked behind an unmarked door, this artful speakeasy is where cocktails arrive with a story, the playlist is always on point, and the retro glassware is swoon-worthy.
The Up Room
2018 W North Ave, Chicago, IL 60647
At the top of The Robey, this rooftop bar is airy, stylish, and boasts wraparound views of the skyline. Expect Mid-century modern décor, floor-to-ceiling windows, and inventive, thoughtfully crafted cocktails.
Kumiko
630 W Lake St, Chicago, IL 60661
Kumiko offers a “fine drinking” experience. Think omakase-style cocktails, Japanese whisky flights, and exquisite glassware in a minimalist, quietly luxe space. A favorite for cocktail connoisseurs and special occasions.
Bisous
938 W Fulton Market, Chicago, IL 60607
A 19060’s Parisian-inspired cocktail bar in Chicago. Need we say more? Velvet booths, moody lighting, and a refined but playful menu of creative, ingredient-forward cocktails and small plates. C’est chic!
Gus’ Sip and Dip
51 W Hubbard St Suite 100, Chicago, IL 60654
Unpretentious, approachable, and a playful, nostalgic approach to drinking culture. See why this spot earned itself a place on the 2026 list of North America’s 50 Best Bars.
TREAT YOURSELF
Discover some of Chicago’s best boutiques. Perfect for finding gifts they’ll love, or a little something for yourself.
P.O.S.H.
613 N State St, Chicago, IL 60654
P.O.S.H. is where European elegance meets vintage whimsy. This beloved boutique, reminiscent of a Parisian flea market, offers an eclectic collection of classic tableware, unique bar tools, charming kitchen gifts, and delightful surprises. Every item is carefully sourced and beautifully displayed.
McShane’s Exchange
2012 N Halsted St, Chicago, IL 60614
McShane’s Exchange is one of Chicago’s best luxury consignment shops. The curated selection includes pristine designer handbags, fine jewelry, and rare accessories from brands like Chanel, Hermès, and Louis Vuitton.
Jayson Home
1885 N Clybourn Ave, Chicago, IL 60614
Jayson Home is a destination for refined, worldly home accessories. Beyond its renowned furniture, the shop features artisanal candles, handblown glassware, decorative objects, and artful coffee table books.
Neighborly
Multiple locations
Celebrate Chicago craftsmanship and conscious living at Neighborly, a modern haven for eco-friendly gifts. Discover locally made art prints, sustainable candles, clever housewares, and small-batch stationery.
Humboldt House
1045 N California Ave, Chicago, IL 60622
An ode to creative Chicago, expect a soulful mix of modern decor, hand-crafted ceramics, luxe textiles, and self-care goods. Humboldt House is where meaningful gifting begins.
OUT AND ABOUT
Dive into Chicago’s vibrant culture with our top picks for must-do experiences. Get ready to explore this charming city. There’s truly something for everyone.
Take in skyline views from Promontory Point
A favorite among locals for picnics and sunset watching. This lakeside spot has a peaceful vibe and dramatic skyline views.
Stroll the 16th Street murals in Pilsen
Walk along the 16th Street rail embankment to spot colorful, ever-changing murals. This two-mile-long outdoor gallery is vibrant, and features work from local and international artists.
Listen to live jazz at Andy’s Jazz Club
This cozy jazz club brings in top local acts nightly. Sip a cocktail and soak up a classic Chicago vibe.
Ride bikes along Major Taylor Trail
Skip the busy lakefront for this greenway that winds through neighborhoods and nature.
Take an architectural boat tour on the Chicago River
Marvel at the city’s stunning skyline and learn the fascinating history behind Chicago’s world-famous architecture.
From Chicago, with love.
- The Irwin team
