Cindy's Rooftop | 12 S Michigan Ave (Loop/Downtown)

https://www.cindysrooftop.com/

Stylish rooftop restaurant with indoor and outdoor seating that overlooks Chicago's Millennium Park, The Bean, and Lake Michigan. Great place to grab a drink!

Federales | 180 N Morgan Street (West Loop)

https://www.federalesfulton.com/

This place is for those of you who want to keep the party going after Puttery on Friday night. Get a shot of tequila in an ice shot glass and ring the bell!

Lou Malnati's | 1120 N State Street (Magnificent Mile)

https://www.loumalnatis.com/

If you want to try deep dish pizza while you're in Chicago, Lou's is a classic. Get The Lou deep dish and house salad to share.

Angela's Burrito Style | 2556 N Clark Street (Lincoln Park)

http://orderangelasburritostyle.com/

Our happy place. We hit up this taqueria at least once a week, and actually, Josh is grabbing takeout from here as Alexa writes this. Our personal favorites are the asada and pastor tacos (with onions and cilantro only), and a side of fries. Trust us.

Millennium Park | 201 E Randolph Street (Loop/Downtown)

https://www.choosechicago.com/articles/parks-outdoors/millennium-park-campus/

A public park in the heart of Chicago's downtown (The Loop), home to the iconic Bean and a Chicago-themed mini golf course (if Puttery wasn't enough for you)! Crown Fountain and Maggie Daley Park are personal favorites, as well.

The Art Institute of Chicago | 111 S Michigan Ave (Loop/Downtown)

https://www.artic.edu/

Located right next to Millennium Park, Chicago's Art Institute is one of the oldest (founded in 1879) and largest museums in the U.S. It's home to a vast collection of art that spans centuries and the globe – including A Sunday on La Grande Jatte (George Seurat), Nightlife (Archibald John Motley Jr.), Under the Wave off Kanagawa (also known as The Great Wave; Katsushika Hokusai 葛飾 北斎), Nighthawks (Edward Hopper), American Gothic (Grant Wood), and many more.

Chicago River Architecture Tour | 400 N Michigan Ave (Magnificent Mile)

https://www.wendellaboats.com/Boat-Tours/chicagos-original-architecture-tour/

A 90-minute tour of Chicago's legendary and eclectic architecture, and the related history...on a boat! The comprehensive tour navigates through the heart of the city on all three branches of the Chicago River. Indoor, climate-controlled seating is available, and tours will be running through November! This sounds like a tourist trap, but trust us, it's not.

Shedd Aquarium | 1200 S DuSable Lake Shore Drive (Museum Campus)

https://www.sheddaquarium.org/

Indoor public aquarium that opened in 1930. Holding 5 million gallons of water and 32,000 animals, it's the third-largest aquarium in the Western Hemisphere, after the Georgia Aquarium and the Monterey Bay Aquarium. Alexa is obsessed with petting the manta rays, but it might be their off-season :/

Lincoln Park Zoo | 2400 N Cannon Drive (Lincoln Park)

https://www.lpzoo.org/

As the site puts it, a wildlife experience in the heart of Chicago. The zoo is open 365 days a year and is always free (no reservations required). In fact, it always has been free since its gates first opened in 1868. {Fun Fact: the rental fee for Café Brauer goes directly towards supporting the Lincoln Park Zoo!}

Lincoln Park Conservatory | 2430 N Cannon Drive (Lincoln Park)

https://www.lincolnparkconservancy.org/projects/conservatory-garden/

A conservatory and botanical garden built between 1890 and 1895 that showcases lush, exotic plants from around the world in four display houses – The Palm House, Orchid House, Fern Room, and Show House. Weather permitting, take a minute to explore the adjoining gardens and catch a glimpse of Chicago's skyline. Admission is free, but reservations are required!