Check-in time. 3pm Friday. Hopefully you had a nice salad or an austere cup of yogurt at O’Hare upon landing, because you have a lot of ground to cover. Get settled in your lovely, lovely room and get organized. There are only so many mealtimes in two days.
4pm. Our beautiful Drawing Room. Grab your charger, plug in your phone at one of the communal tables and gather your group for happy hour and a strategy session. Perhaps your cocktail go-to should be the Colt .59? The combination of whiskey, coffee liqueur, sherry, absinthe and bitters is sure to give you the jolt of inspiration and energy needed. Pro tip – no one ever said a Chicago Style Footlong couldn’t be an appetizer. Order it to share – this authentic dish is served ‘Dragged Through The Garden’ – if you know, you know. Now you’ve got one must-have already checked off.
5:44pm. Hop your Lyft (or leave 15 minutes earlier and jump the Brown line going north for a beautiful ride through the Loop, over the river and north through the city) to Lincoln Park and arrive at Galit – a newly Michelin-Starred Middle Eastern Restaurant with a menu that is ‘a 4-course choose your own adventure.’ The menu focuses on a seasonal and localized approach to dishes of the Middle East and Israel’s immigrant cuisines. Luckily, you booked this one ahead.
10pm. The Milk Room. Lucky you ALSO booked this 8-seat cocktail bar exactly one month ago tonight (reservations open one month in advance and slots go fast), and extra luckily, you are already home when you get there as it is located under our storied roof. This former speakeasy boasts a spirit-forward cocktail menu crafted from the rarest vintage spirits and elixirs. You will never forget your time here.
Saturday morning. 8:15 wakeup. Make that 8:45. Grab the perfect morning beverage at Fairgrounds in the lobby and head out to Millenium Park to clear your head. Walk around and enjoy the art and nature until your stomach starts to growl. And then quick – jump in a cab up scenic Lake Shore Drive to the 2d Restaurant. This Instagram-able spot serves mochi donuts in high style – the entire store is a monochromatic illustration. You have to see it to get it so go. Hold yourself back from ordering one of their chicken sandwiches. This is not the path for you, young Jedi. You have lunch plans.
11:30am. Hop on a Divvy bike (Chicago’s bike share program) for a 23-minute ride to super-hip Wicker Park. Time for lunch at Phodega where Pho and Hainanese chicken rice are menu favorites. Purchase some Asian snacks for late night munching in your room on your way out and head off on foot to explore this vibrant neighborhood (and walk off your last two meals.) You have until 4:45pm. Get those steps in.
5pm. Oh joy – you made a reservation right at opening at The Violet Hour for an elegant, relaxing and well-earned cocktail. This iconic destination for cocktail enthusiasts has a seasonally rotating cocktail list and an ever-changing mural at its discrete single entryway. Don’t get too comfortable. (This will probably be hard.)
6:15pm. Hop a car back to your historic home-away-from-home and scoot up to your room for a shower and a change. Tonight’s the night. You booked Cindy’s – our Great Lakes-themed rooftop destination with the gorgeous view and the Warhol – for tonight’s big meal. And you get to enjoy this amazing experience with the knowledge that your comfy bed is just an elevator ride away. You win! Toddle up to Cindy’s for your 7pm reservation. Enjoy.
9pm. Well that was exhilarating. Maybe it’s time for the winning to continue. Off to the Game Room for a round of bocce ball before bed. Do not order another Chicago Style Footlong for dessert. Don’t. Do. It. Just wait and order Shake Shack as a night cap in your room.
Sunday. 8:30am. Maybe make it 9am. Hop a car (or borrow the hotel’s Heritage bikes if they’re out for the season) and head to The Duck Inn. This staple is at the border of Pilsen and Bridgeport right on the river and has an award-winning Sunday brunch. Sunday is also industry day – industry and artists eat for 50 percent off and are invited to bring records to play on the vintage turntable console so the scene is sure to be the real deal. Finish brunch, and off to explore the neighborhood.
11am. Panaderia Nuevo Leon. Pick up some pastel-pink conchas to take home to share with those less fortunate you left at home. Don’t forget to add some Polvoron – shortbread cookies shaped like a pig. Hop a car back to us for your noon checkout time.
12:30. Jump the Blue Line for O’Hare. Feel a wistful sadness – sigh – your culinary adventure is coming to an end. BUT WAIT! The Chicago King of Mexican Cuisine Rick Bayless does not want you to be sad. All is not lost. No matter what gate your flight takes off from, head to Terminal 1, 3 or 5 to enjoy one last Chicago culinary memory – Tortas Frontera has hand-shaken margaritas, fresh made guacamole and delicious tortas. Not your typical airport food. But, after all, Chicago’s not your typical town.
Ready to spend 48 hours feasting in Chicago? We’ve got you covered.