Chicago Travel Guide · Jano Septien

A collection of hidden gems, standout restaurants, and cozy cafes across Chicago's neighborhoods, gathered from saved Instagram finds.

Food & Drink

Hallowed Grounds: UChicago student-run coffee shop and food hall in Hyde Park. Gothic architecture with ornate wood ceiling, crystal chandeliers, decorated walls with portraits. Menu includes espresso drinks, iced beverages, chai, matcha, pastries. A “sacred meeting place” you have to know about to find; great for studying, with pool/billiards tables and lounge seating. reel
Drawing Room: Second-floor lounge overlooking Michigan Avenue. Vintage/retro aesthetic with warm lighting, elegant furniture, sophisticated atmosphere. Located inside a historic building that appears private but is publicly accessible; walk in and take the stairs, no permission needed. reel

Riverwalk dining (ranked):

Best restaurants by occasion:

Unique coffee shops:

The Foyer Café: Downtown favorite; serves coffee and pastries. reel
Botanical Cafe: Plant shop combined with cafe; surrounded by greenery. reel
Bad Coffee: Hidden in an alley; specialty coffee. reel
Charmers Cafe: Food & floral cafe; colorful, artistic window displays. reel
Nabala Cafe: Turkish coffee and Palestinian treats; modern interior with gallery wall art. reel
MeLatte Coffee Shop: Coffee, crepes, and local art; vibrant vintage-inspired seating. reel
City Skyline: Aviation-themed cafe with jellyfish sculpture and aircraft decor. reel
Volumes Bookcafe: Bookstore & cafe combination; extensive book collection and board games. reel
Frera Desserts: Plant-based desserts; features creme brûlée torching at tables. reel

5 hidden gems:

Caché: French-inspired hidden cocktail lounge/speakeasy with craft cocktails; requires discovery/advance knowledge to find. reel
Dot’s: New coffee shop in Roscoe Village; serves coffee and specialty drinks, newly opened. reel
Caña: Coffee and cocktail lounge; serves cold brew, mocktails, avo aquas (avocado water refresher). reel
Crying Tiger: Vibrant Southeast Asian restaurant with noodle dishes and craft cocktails. reel

UChicago Campus - Hyde Park: Contains Hallowed Grounds and other recreational facilities; serves students and public visitors. reel
12 S Michigan Ave, Chicago, IL 60603: Historic building housing the Drawing Room lounge. Red brick and cream-colored facade with distinctive architectural details including ornate window patterns; ground floor has retail/restaurant spaces. reel
Lost Soul Found: Boutique & coffee shop; home goods and jewelry displays. reel
Elston Electric: Arcade bar with vintage arcade games and fun atmosphere. reel
Afterwords Bookstore: Located in River North. Hidden gem independent bookstore with over 70,000 new and used books; basement section great for browsing. One of few remaining independent bookstores in downtown Chicago. reel
Ravenswood Used Books: Feels like a maze with rare and vintage books; cozy nooks for reading. Super affordable, great for tight budgets. reel
Sandy Meyer’s Bookstore: Family-owned shop operating since the early 1980s. Carries newest and most popular titles; hosts an active book club community. reel
Barnes & Noble Wicker Park: Visually stunning bookstore with ornate coffered ceilings, decorative skylights with blue star designs, tall windows, and brass pendant lighting. Notable travel books section on the upper floor. Exterior appears plain, but interior is beautifully decorated, great for photos. reel

Chicago’s riverwalk has many tourist traps; use rankings/reviews to find quality dining, and consider boat access and waterfront ambiance when choosing a spot. reel
For restaurant hunting by neighborhood: West Loop for trendy spots (Monteverde, Au Cheval), Chinatown for budget-friendly eats (Chiu Quon Bakery), Bucktown and Pilsen for affordable tacos/street food, Lincoln Park for options across price points, and River North/Fulton Market for both casual and celebration-worthy dining. reel
Hallowed Grounds is a hidden gem at UChicago: you need to know it exists to find it; not a casual walk-in spot. reel
Chicago’s coffee shop scene is diverse. Plan a cafe-hopping itinerary by neighborhood, choosing spots based on theme (botanical, artistic, bookish, aviation, etc.); many double as boutiques and are highly photogenic. reel
The Drawing Room lounge is easily walkable and centrally located on Michigan Avenue. Most tourists and locals walk right past it, but you can simply walk in and take the stairs to the second floor. reel
Support Chicago’s independent bookstores; all three (Afterwords, Ravenswood, Sandy Meyer’s) are locally-owned small businesses worth visiting for summer reads. reel
Caché speakeasy requires advance discovery/knowledge to find; Dot’s in Roscoe Village is newly opened and worth checking for coffee enthusiasts. reel