Sometimes a trick to get a reservation (very chic, popular), Cindy's hosts the best open air views of Millennium Park. At a minimum, pop up to the no-reservation bar and grab a cocktail and a peek at Chicago. Alternative amazing views of the Chicago River are found at London House and Trump Tower (if you can stand it).
Less specific about this restaurant and more specific about a visit to Chicago's Riverwalk, the path that runs by City Winery is a lovely place to go for a walk, morning jog, enjoy nearby takeaway (Pastoral, Goddess & the Grocer, Protein Bar, Lyfe Kitchen). Not crazy about the wine at City Winery (oddly enough), it is a nice place to stop for a drink, snap a photo of the famous 'Blues Brothers' House of Blues, and watch the activity on the river.
Mario Batali's superstore overflows with the a to z of Italian cuisine. Stop by the wine shop or purchase a bottle of wine at any eatery and carry as you adventure through the crudo bar, antipasti bar, or one of the many restaurants (pizza/pasta, fish, meat, etc). Finish things off over gelato, nutella or espresso on the first floor.
Alive/happening any night of the week, this area has become the 'it' spot over the last 5 yrs for dining and cocktailing in Chicago. Favorite spots for drinks include: Soho House, Cruz Blanca, The Aviary (SERIOUS mixology - look into reservation), Momotaro Izakaya, The Betty, Moneygun. Favorite spots for lunch/dinner include: avec (Melinda's favorite restaurant in Chicago), Blackbird, Girl & the Goat (Jason's favorite restaurant in Chicago), The Publican, Roister, Momotaro, Bad Hunter, Lena Brava. Elske took Bon Appetit's #2 best new restaurant opening in the U.S. (the husband-wife team came from Blackbird's kitchen).
Rick Bayless is a King in Chicago, known for fantastic authentic Mexican and dangerous Blue Agave margaritas (a must!). Located in the happening River North neighborhood, reservations are limited, lines are typically long, but put your name on the list (the queue to get on the list begins at 4:30p for dinner, they'll text you when your table is ready) and you won't be disappointed. If only two of you, don't discount dining at the bar either; the margs and chips are just as delicious. ;-)
Capacity is 55, reservations are extremely limited and tables are communal, but pop in, put your name on the list for two seats at the bar and walk around the corner to Proxi, Sepia or over the hwy to Soho House's The Allis and enjoy a cocktail (or two) as you wait for the text regarding your seat. avec is Melinda's favorite restaurant in Chicago.
Quintessential sophisticated dining on Randolph Row. Open for 20 years, they are consistently recognized for their service and fine seasonal food (don't miss the endive salad -- served in a potato 'basket' and topped with a poached egg, it's more of a clever Blackbird 'nest')
Located in the chic Gold Coast, Italian seafood-focused Nico is as delicious as it is fun. If you can't get a reservation, put your name on the list and enjoy a cocktail (or two) in the Nico Salone, which is the ideal combination of comfort and scene (also a great place to order starters). Also, the chef's bar in Nico is ideal if you are only two -- we love to watch the team at work!
For those here before the weekend (only open M-F), a great stop to sample several Chicago restaurants under one roof. Don't miss the brisket at Smoque BBQ or sweets from Mindy's Hot Chocolate!
Located in a historic building in the Gold Coast, this is a magnificent place to enjoy a beverage (coffee or glass of wine). Four floors of Restoration Hardware showroom furniture, you can grab on a drink on the first floor and get comfortable on a couch on any floor, or, better, head up to the roof for a beautiful, relaxed setting There is a dining room/restaurant on the first floor, which is gorgeous, but the wait for a table is always so long and the food, while good, never seems worth the effort.
A nightlife recommendation in River North, enter at your own risk. This place is HUGE! Different music in several rooms, often something live, this place is always hopping! I probably wouldn't plan dinner there (though they have a full menu and it is good), but it's a place for lively cocktails...
A country western bar in River North (around the corner from Untitled), the vibe is casual and relaxed in this intimate space that hosts live country music. The BBQ is good -- pulled pork sandwiches, etc -- and peanut shells always litter the floor.