Growing up only a few hours away from Chicago gave us the opportunity to visit throughout the years. There are several lists out there highlighting tourist attractions however we wanted to specially curate a list of our go-to's that incorporate both well known and local favorites. So next time you are planning to visit the windy city for the weekend, make sure to bookmark this guide - we're sure you will love these places as much as we do.
8:30 am | Wake up at The Robey - a midcentury modern inspired hotel with special amenities like a rooftop bar and balcony grotto, which make it hard to leave. Standing tall at 203 ft and with 89 rooms the Robey may be one of the newer hotels to the area but its quickly becoming a favorite. We recommend grabbing the avocado toast and an americano at Café Robey to fuel up for your day.
Not only known for their excellent customer service and views of downtown but the Robey has 3 bars and 1 café that can attend to all your foodie needs. At night our favorite was grabbing a drink at the Up Room which has a rooftop terrace showcasing the Chicago skyline.
9:30 am | Step out of the hustle and bustle of the city to the Garfield Conservatory, where you are instantly surrounded by lush greenery and tranquil fountains. Going in the morning is your best bet for finding quiet and stillness before tourists start pouring in. Check their calendar for complementary yoga classes on certain mornings.
11:00 am | If Morocco and Anthropologie had a restaurant baby, Beatnik would be it. Even before you step inside, you know that the Beatnik is more than just a spot to eat... it's a whole experience. Pro tip | order the cinnamon chai roll.
12:30 pm | We love Heritage Outpost, a coffee and bike shop. I don't know what it is about these two but they work so well together. Maybe it's that grab-a-cup of coffee and go vibe but we're hoping we get one in Detroit very soon.
2:00 pm | After reaching out to the Instagram community we quickly learned from most that Nini's was a must stop local favorite. The story is like most in Chicago, immigrants hoping to create a life surrounded by their culture and passions. Known for their classic Cuban sandwiches, you will feel immediately connected to their families story and heritage. highly recommend getting the Ropa Vieja burrito and the Café con leche. Pro Tip | Hot Cheeto Elote, order it, live by it, love it
Head back to The Robey for a quick power nap or to freshen up before dinner and drinks.
5:30 pm | Midwest living means spring is nothing but another season of what if's. Celeste offers a rooftop garden vibe enclosed though so it can be enjoyed all year round. A deco inspired patio with large lounge chairs make up for intimate conversation and we loved the soft lighting and the bountiful amount of plants.
7:30 | Bellemore isn't just a new restaurant; it evokes a sense of newance as soon as you walk in. Elevated ceilings with walls adorned with stark whites and dark wood tones, the aesthetic will leave you wanting to renovate your own home décor. The food quickly showcases the level of artistry that the Bellemore is known for, with simple dishes that take on a complex elegance.
9:30 | Head to this upstairs hidden cocktail lounge and you'll quickly learn that this spot is so much more than just drinks. Bordel is known for it's cabaret shows throughout the night, with dark lighting and velvet seating. The Parisian style ambiance takes you to a time where late nights turn into morning hours and before you know it you're spilling into the streets with the memories of a great night. Pro Tip | Their signature cocktail is the porron, which is a Spanish wine pitcher, it's a whole experience.
9:30 am | Located in the Waldorf Astoria, Margeaux Brasserie mixes upscale vintage with a Parisian café. Indulge in a decadent brunch as you sip rose from their cart and sit in deep booths with dark wood paneling. Pro tip | if you have any stomach room left splurge for the cheese cart, its worth it.
11:30 am | When you need a quick fix for your sweet tooth head to Doughnut Vault, they create small batches of artisanal donuts that will leave you indecisive on your top choice. Pro tip | Order the special of the day. they are listed weekly on their website.
12:00 pm | Recently voted the #1 museum in the world by Trip Advisor, The Art Institute of Chicago has over 182 exhibits that call this space home. Where endless rooms of contemporary art quickly meld into impressionist and sculptural pieces from west and central Africa stand tall. We quickly lost track of time as we were transported to another era.
2:30 pm | We could have stayed all day at The Allis- and we almost did. Soho House's street level dining is one of the few restaurants within the club that are open to the public. Comfortable seating below massive chandeliers set the mood for their well known tea service. Pro Tip | get a bloody mary and the warm coconut (vegan!) pudding.
4:00 pm | Disclaimer; Cindy's does not allow photographs of the interior but I snuck this one of the incredible view they have, It was a cold day but it was worth it. This spot is always hustling and bustling as it sits across from the Art Institute and is known for its incredible views of the lake and downtown. Its a rooftop bar which boasts a lively crowd and the perfect craft cocktails.
Head back to the Robey to freshen up and head to the Up Room for a pre dinner cocktail.
7:30 pm | RPM Italian isn't one of the new kids, its a part of an entire group of restaurants in Chicago and we cant help but love them all. We recommend making reservation here as it's always busy. We decided to order a variety of dishes as we had a larger group and wanted to indulge family-style. Pro Tip | Always ask the staff for their recommendations, they know best!
9:30 pm | End the night with an artisanal cocktail at Violet Hour. This speakeasy spot doesn't allow standing room so make sure to get there early. The cocktail menu is constantly changing so step out of your comfort zone and be a little adventurous with your choice.
Thank you to the teams of: Bonhomme group, Waldorf Astoria, The Robey and Lettuce Entertain You for hosting us these past 48 hours.
on to the next city!