Cindy’s Rooftop is a fun and relaxing place to eat and drink in downtown Chicago. It is located on top of the Chicago Athletic Association Hotel and gives you amazing views of the city skyline, Lake Michigan, and Millennium Park. The food here is fresh and seasonal, and the drinks are colorful and creative. People love coming here for brunch, dinner, or just to enjoy the rooftop view.
The space feels open, bright, and full of life. If you are looking for a great rooftop restaurant in Chicago, Cindy’s Rooftop is a perfect choice.
History and Concept of Cindy’s Rooftop
Opened in 2015, Cindy’s Rooftop became an instant favorite for locals and visitors. The name and ambiance reflect a warm, welcoming spirit, like visiting a stylish relative’s home with panoramic views.
Housed in the historic Chicago Athletic Association Hotel, the rooftop was created to combine culinary creativity, thoughtful design, and hospitality excellence.
Cindy’s Rooftop Menu With Prices
The menu is seasonal, locally inspired, and full of flavor. Cindy’s offers dishes that change throughout the year to reflect fresh, regional ingredients.
Must-Try Dishes
- Lobster Roll with light dressing and house-made chips
- Caviar-Topped Deviled Eggs for a luxurious appetizer
- Sunday Fried Chicken with honey butter and pickles
- Roasted Cauliflower Salad, a hearty vegetarian delight
- Crispy Skin Salmon with Lemon Vinaigrette
- Oysters on the Half Shell from the raw bar
Vegan guests love the charred broccoli and beet salad, while gluten-free diners can enjoy many dishes by request.
Lunch Menu
Available M-F, until 2 pm
Starters (Additional Items)
| Item | Price | Description | Dietary Info |
| DRESSED BEAU SOLEIL OYSTERS* | 24/48 | pickled shallot & champagne mignonette | gf, nf, df |
| SMOKED WHITEFISH DIP | 19 | cucumber, herbs, grilled sourdough | nf |
| TRUFFLED DEVILED EGGS | 15 | – | v, nf, df, gf |
For April, $1 from every oyster ordered will be donated to March of Dimes.
Salads
| Item | Price | Description | Dietary Info |
| CAESAR SALAD* | 19 | little gem lettuce, herby breadcrumbs, parmesan | nf |
| BARLEY BOWL | 16 | bok choy, avocado, shiitake, carrot, kimchi, tahini-ginger vinaigrette | vg, nf |
| BIBB SALAD | 19 | maple bacon, hard-boiled egg, tomato, buttermilk dressing | gf, nf |
Salad Add-Ons:
- Avocado (+$5)
- Chicken (+$10)
- Grilled shrimp (+$12)
- Salmon* (+$13)
Entrées (Additional Items)
| Item | Price | Description | Dietary Info |
| FRIED CHICKEN SLIDERS | 24 | pimento cheese spread, coleslaw, brioche, malt vinegar potato chips | nf |
| CHEESEBURGER* | 26 | aged Wisconsin cheddar, LTO, pickle, special sauce, brioche bun, house fries | nf |
| LOBSTER ROLL | 34 | warm brioche, malt vinegar potato chips | nf |
| STEAK FRITES* | 62 | 10oz skirt steak cap, house fries, brown butter hollandaise & aleppo pepper | gf, nf |
NOTES
- Surcharge: A 4% fee is added to checks to offset rising costs (can be removed upon request).
- Dietary Key:
- V = Vegetarian | VG = Vegan | NF = Nut-Free | DF = Dairy-Free | GF = Gluten-Free
Dinner Menu
Available 5 pm – 1 pm
Entrées
| Item | Price | Description | Dietary Info |
| ASPARAGUS | 28 | potato, black truffle, watercress & smoked butter | v, gf, nf |
| CACIO E PEPE | 28 | hand cut tagliatelle | v, nf |
| GREEN CURRY PRAWNS | 39 | chorizo, coconut milk, cilantro, basil, ginger, grilled sourdough | nf |
| HERITAGE BRICK CHICKEN | 42 | calabrian chili, chicken jus vinaigrette, tarragon yogurt | gf, nf |
| STEAK FRITES* | 62 | 10oz skirt prime steak cap, house fries, brown butter hollandaise & aleppo pepper | gf, nf |
| FILET MIGNON* | 62 | 6oz prime tenderloin, morels, english peas, bone marrow bordelaise sauce | gf, nf |
To Share
| Item | Price | Description | Dietary Info |
| BEAU SOLEIL OYSTERS* | 24/48 | pickled shallot & champagne mignonette | gf, nf, df |
| SMOKED WHITEFISH DIP | 19 | cucumber, herbs, grilled sourdough | nf |
| PARKER HOUSE ROLLS | 15 | french butter, maldon | v, nf |
| TRUFFLE DEVILED EGGS | 15 | – | v, nf, df, gf |
| GRILLED ARTICHOKES* | 17 | fines herbes aioli, fried capers | v, nf, df, gf |
| CURRIED CARROTS | 16 | yogurt, cumin oil, duck skin crumble | gf, nf |
Salads
| Item | Price | Description | Dietary Info |
| BIBB SALAD | 19 | maple bacon, hard-boiled egg, tomato, buttermilk dressing | gf, nf |
| CAESAR SALAD* | 19 | little gem lettuce, brioche croutons, parmesan | nf |
Desserts
| Item | Price | Description | Dietary Info |
| CHOCOLATE CHIP COOKIES | 12 | freshly baked, maldon | v, nf |
| SEASONAL SCOOPS | 6 | sorbet: lemon-rosemary ice creams: vanilla or raspberry-pistachio | sorbet: vg, nf, gf vanilla: v, nf, gf raspberry: v, gf |
| STRAWBERRY MOUSSE | 15 | passion fruit, basil ice cream, brown butter sablè | gf, nf |
| SUMMER BERRY TARTE | 15 | citrus cream, blackberry compote, clotted cream ice cream | v, nf |
| COCONUT PECAN CHOCOLATE CAKE | 16 | death by chocolate cake, coconut pecan milk chocolate ganache, roasted cacao nib ice cream | gf |
Beverages Menu
Cocktails ($18 each)
Curated By Kylie McCalla & Cindy’s Bar Team
| Cocktail Name | Description | Flavor Profile | Notes |
| NO SOUP FOR YOU | lemongrass, galangal, makrut lime spirit, tamarind smirnoff, thai chile, soda | savory – tangy – spicy | – |
| *KOKOMO | botanist gin, passionfruit, pecan, lime, demerara, angostura bitters | tropical – nutty – acid | *contains nuts |
| ONE EYE ONE HORN | rum & cachaca, bitter bianca, pineapple shrub, cinnamon, ube | purple – tannic – saccharine | – |
| JALISCO HAZE | el tesoro reposado tequila, allspice dram, garam masala, lime, mint, angostura bitters | curry spice – herbal – refreshing | – |
| HELICOPTER PEARENTING | del maguey vida mezcal, spiced pear, absinthe, lemon | seasonal – medicinal – smoky | – |
| PEAT & FOG | glenfiddich 12yr sherry cask scotch, vermouth, cherry cappelletti, scarborough bitters | mulled – vegetal – peaty | – |
| SCHMOKE & A PANCAKE | apple brandy, mezcal, montenegro, cynar, black strap rum, mole bitters | smoke – maple – chili | – |
| DEEP WOODS | woodford reserve bourbon, amaro dell’etna, sfumato, piloncillo, chocolate bitters | alpine – wood – cocoa | – |
Spirit-Free (Non-Alcoholic)
+ add 10mg CBD for $3 (must be 18+)
| Item | Price | Description | Flavor Profile |
| UPSIDE DAWN (Athletic Brewing Co.) | 8 | Non-alcoholic | – |
| LAGUNITAS HOPPY WATER | 10 | Sparkling hoppy beverage (Citra, Equinox, Centennial hops) | crisp – zingy |
| BOULEVARDI-NAY | 12 | Lyre’s Italian Spritz, American Malt, Lucano Zero, demerara, lemon | spice – botanical – wood |
| MISS AMERICAN PIE | 12 | Ritual tequila, Seedlip spice, apple pie, lemon, ginger | bright – spicy – crisp |
| TAKEN BY THE WIND | 12 | Almave blanco, chamomile lavender orange, lime, elderflower tonic | floral – fresh – cool |
| FREE SPIRIT SPRITZ | 12 | Lyre’s Italian Spritz, alcohol-removed prosecco, soda | bitter – bubbly – pith |
| MIONETTO “ALCOHOL REMOVED” (Sparkling Wine) | 10/40 | Veneto, Italy | – |
Coffee & Tea
| Item | Price |
| Drip Coffee | 4 |
| Espresso | 5 |
| Iced Estate Black Tea | 5 |
| Latte/Cappuccino | 6 |
| Matcha Latte | 8 |
| Kyoto Black Cold Brew | 7 |
Rare Tea Cellars ($8):
- Crema Earl Grey
- Cloud Kissed Green
- Regal English Breakfast
- Mint Meritage (caffeine-free)
- Emperor’s Chamomile (caffeine-free)
Brunch Specialties
| Item | Price | Notes |
| DIY MIMOSA | 75 | Francois Montand Brut NV (Jura, France) + fresh berries/juice |
| Champagne Drappier ‘Carte d’Or’ NV (Aube, France) | 125 | – |
| *Spirit-Free DIY Mimosa | 75 | – |
| BLOODY MARY | 16 | Choice of: Titos vodka, mezcal unión, linie aquavit |
| *Spirit-Free Bloody Mary (Seedlip Garden) | 12 | – |
| QAHWA COFFEE | 18 | Reyka vodka, broghetti, Kyoto cold brew, demerara, green cardamom (add cream/DF milk) |
Brunch at Cindy’s Rooftop
Weekend brunch at Cindy’s is a must. The atmosphere is lively, and the sun pours in through the glass ceiling.
Available Saturdays and Sundays, until 2 pm
Starters
| Item | Price | Description | Dietary Info |
| BEAU SOLEIL OYSTERS* | 24/48 | pickled shallot & champagne mignonette | gf, nf, df |
| GRANOLA BOWL | 16 | house granola, maple, Greek yogurt, berries | v, gf, nf |
| AVOCADO TOAST | 23 | kale pesto, pickled fresno & shallot, sundried tomato, parmesan, sourdough | v, nf |
| SMOKED SALMON | 23 | dill cream cheese, cucumber, pickled onion, caper, everything bagel | nf |
| CAESAR SALAD* | 19 | little gem lettuce, herby breadcrumbs, parmesan | nf |
Note: For April, $1 from every oyster ordered will be donated to March of Dimes.
Classic Breakfast
| Item | Price | Description | Dietary Info |
| CLASSIC BREAKFAST* | 24 | choice of chicken sausage or Nueske’s bacon, scrambled eggs, breakfast potatoes | gf, nf, df |
Eggs & Entrées
| Item | Price | Description | Dietary Info |
| CHILAQUILES* | 25 | salsa roja, chorizo, queso fresco, crema, fried eggs (+add prime skirt steak 14) | gf, nf |
| EGGS BENEDICT* | 26 | English muffin, prosciutto cotto, brown butter hollandaise | nf |
| ‘BANANAS FOSTER’ FRENCH TOAST | 23 | brioche, pecans, whipped crème fraîche, rum butter syrup | v |
| CHEESEBURGER* | 26 | aged Wisconsin cheddar, LTO, pickle, special sauce, brioche bun, house fries | nf |
Sides
| Item | Price |
| NUESKE’S BACON | 9 |
| CHICKEN SAUSAGE | 6 |
| BREAKFAST POTATOES | 8 |
| TOAST | 7 |
| BERRIES | 8 |
Pastries
| Item | Price | Description | Dietary Info |
| CROISSANT | 8 | housemade jam, whipped butter | v, nf |
| MONKEY BREAD | 15 | cream cheese glaze (to share) | v, nf |
Brunch Favorites
- Dutch Baby Pancakes with berries and syrup
- Avocado Toast with microgreens and pickled onions
- Vegetable Frittata with seasonal vegetables
- Fried Chicken and Biscuit with spicy honey drizzle
Add a Mimosa Flight or Bloody Mary for a complete rooftop brunch experience.
Location and Atmosphere
Located at 12 South Michigan Avenue, Cindy’s offers one of the best rooftop views in Chicago. Guests can see Millennium Park, Lake Michigan, and even the Art Institute from their table.
Inside, Cindy’s has a greenhouse-inspired space filled with natural light, hanging plants, and cozy furnishings. Outside, the open-air terrace features fire pits, heaters, and plush seating—perfect for all seasons.
Best Times to Visit
The vibe at Cindy’s changes with the hour. Timing your visit can make all the difference.
Popular Hours
- Weekend brunch (make reservations early)
- Golden hour before sunset for photos and views
- Evenings during fireworks or events on the lakefront
Quieter Times
- Weekday lunch
- Late afternoons before dinner
- Weeknights during colder months (indoor ambiance still shines)
Cindy’s Rooftop Reservations and Booking Info
Book your table on Cindy’s Rooftop or through OpenTable. Reservations are highly recommended for peak times.
Private Events
Cindy hosts events like:
- Rehearsal dinners
- Corporate gatherings
- Birthday celebrations
The private space offers custom menus, event planning, and incredible views.
5 Reasons Cindy’s Rooftop is the Best Skyline Dining Experience in Chicago
Cindy’s Rooftop is more than a meal. It is an experience.
- Breathtaking City Views: Enjoy panoramic vistas of Chicago’s skyline and Lake Michigan from Cindy’s Rooftop, creating the perfect backdrop for any occasion.
- Seasonal American Cuisine: Savor fresh, locally-sourced dishes crafted with seasonal ingredients, offering a delicious taste of modern American flavors.
- Handcrafted Cocktails: Delight in creative, expertly mixed cocktails that pair perfectly with the vibrant atmosphere and stunning views.
- Chic Ambiance: Experience a stylish yet welcoming vibe, where modern design meets cozy elegance, making it ideal for date nights or group gatherings.
- Unmatched Location: Situated in the heart of Chicago, Cindy’s Rooftop combines convenience with luxury, making it a must-visit destination for locals and tourists alike.
This list highlights the unique selling points of Cindy’s Rooftop while incorporating power words like “Breathtaking,” “Delight,” and “Unmatched” to create excitement and engagement. 🍹🌆✨
Tips for First-Time Visitors
Dress Code:
Smart casual. Dress up a bit to match the ambiance. Avoid athletic wear.
Weather Advice:
The terrace has heaters, but indoor seating still offers stunning views.
Transportation:
Take public transit or a rideshare. Paid parking garages nearby can be expensive.
Photo Tip:
Arrive 30 minutes before sunset for the best photos. The lighting is perfect.
Location on Map:
Quick Guide About Cindy’s Rooftop
| Category | Details |
| Google Rating | 4.5 (⭐⭐⭐⭐) (4,906 reviews) |
| Price Range | $30-50 |
| Type | Restaurant |
| Location | 12 S Michigan Ave, Chicago, IL 60603, United States Floor 4 · Chicago Athletic Association – The Unbound Collection by Hyatt |
| Coordinates | V9JG+M2 Chicago, Illinois, USA |
| Description | Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare. |
| Services | Dine-in · Takeaway · Delivery |
| Hours | 10 am–11 pm |
| Website | For Cindy’s Rooftop menu with prices, visit the official website here. |
| Phone | +1 312-792-3502 |
| Features | LGBTQ+ friendly |
Cindy’s Rooftop Reviews
Overall Google ratings: 4.5/5 (⭐⭐⭐⭐⭐) Based on 4,906 reviews
i) Ashley W: 5/5 (⭐⭐⭐⭐⭐) (04-20-2025)
Visited for Dinner · Budget: $50–$100
Cindy’s Rooftop sits on top of a hotel and offers both indoor and outdoor seating. It is a popular spot, so making a reservation is a must. The vibe feels fancy but still relaxed. The menu is not very large, but it has a nice variety of choices.
Our server was friendly and really knew the menu well. One of our friends has a gluten allergy and cannot have citrus, but the server explained everything clearly. She was able to order with no worries. The food was tasty, but the dessert menu could use more variety.
Tip: Arrive early before your reservation and grab a drink at the Game Room on the hotel’s second floor.
Food: ★★★★★
Service: ★★★★★
Atmosphere: ★★★★★Dietary Notes: Good options for gluten-free and nut-free diets.
Parking: It can be hard to find parking nearby.
ii) Ben R: 5/5 (⭐⭐⭐⭐⭐) (04-06-2025)
Visited for Brunch · Budget: $30–$50
The rooftop has a stunning setting with amazing views of Millennium Park and Lake Michigan. We arrived early and had to wait because the elevator to Cindy’s only opens when the restaurant does. It gave us time to explore the beautiful space.
Brunch was amazing. The food was delicious, and the place was full of light and charm. Service was kind and helpful without being too much.
We tried the chef’s special donut, the seasonal quiche, and the biscuits and gravy. All of it was fresh and tasty. The coffee was hot, and the orange juice and mimosas were refreshing.
Food: ★★★★★
Service: ★★★★★
Atmosphere: ★★★★★
For more reviews and ratings, visit Google Reviews.
Connect With Cindy’s Rooftop
Stay updated on events and specials:
- Instagram: @CindysRooftop
- Facebook: @CindysRooftop
- Twitter: @CindysRooftop
FAQs
Is Cindy’s Rooftop kid-friendly?
Yes. While the ambiance suits adults, children are welcome during brunch and lunch hours.
Can I visit just for drinks?
Yes. You can enjoy cocktails at the bar or terrace without dining.
Is there a dress code?
Smart casual is recommended. Many guests dress up a little for the rooftop setting.
Does Cindy’s accommodate dietary restrictions?
Yes. Vegan, vegetarian, and gluten-free options are available. Notify staff when booking.
What is the best time to get a good photo?
Sunset is ideal. The golden hour lights up the skyline beautifully.
Conclusion
Cindy’s Rooftop is one of the best places to dine and drink in Chicago. From its panoramic views to its flavorful seasonal dishes and Instagram-worthy cocktails, it delivers a top-tier experience.
Whether you are a local or visiting for the first time, Cindy’s belongs on your list. Reserve your table today at cindysrooftop.com and discover why this rooftop continues to capture hearts and photos across the city.
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