For the best views and a dose of Chicago history, hop on an architecture riverboat tour! Our favorite is run by the Chicago Architecture Center.
Visit the iconic Chicago Bean, stroll Lurie Garden, walk over to Maggie Daley Park, and then head south to Buckingham Fountain for classic skyline views.
Head to Cindy’s rooftop for a cocktail and one of the best views of the Bean and the lakefront.
Catch a comedy show at the famous training ground of some of the biggest names in comedy.
One of the world’s great museums and home to iconic works like American Gothic and Nighthawks.
A speakeasy‑style venue with fun, immersive magic shows and great cocktails.
This is Alli's favorite deep-dish in the city. Pro-tip: don't forget the giardiniera!
For an essential Chicago bite, visit Portillo’s: home of the fully loaded Chicago hot dog, hearty Italian beef, and the famous cake shake.
Our favorite restaurant! Serves mediterranean food in the heart of West Loop - a bustling neighborhood full of some of the city's best food and drink spots.
Enjoy Spanish tapas at Café Ba‑Ba‑Reeba, one of Alli's DePaul go‑tos. Get a pitcher of sangria… trust us.
Head to Duck Duck Goat for inventive Asian‑style shared plates from Chicago’s own celebrated chef Stephanie Izard.
Go for a Depression Dog and fries—Mike’s go‑to and an easy stop heading to or from the airport.
Stop by the Wiener’s Circle for a classic Chicago dog served with a side of unforgettable sass.
Mott St serves incredible Asian dishes, but insiders know to hit the bar for their award‑winning burger.
Stop by Gilt Bar for a warm, dimly lit atmosphere, great martinis, and comfort‑style dishes.
Award-wining pastries and coffee in Wicker Park - a fun, artistic neighborhood!
Stop by Ann Sather’s for a cozy Swedish breakfast and their iconic, gooey cinnamon rolls.
Check out Blind Barber, a barbershop‑turned‑speakeasy known for its cocktails, cozy vibe, and live music.
A chic neighborhood cocktail bar.
Stop by Guthries, our beloved neighborhood bar with quirky ceiling art and plenty of board games to grab and play.