Jacqueline & Dylan
Things To Do
Lincoln Park
One of our favorite outdoor spaces in Chicago. On a nice day, we recommend grabbing a coffee from Cocoa + Co., Foxtrot or La Fournette and walking through the Nature Boardwalk and the Lincoln Park Zoo. (P.S. the Zoo is free!!)
Lakefront Trail
An iconic Chicago experience. There are over 18 miles of bike and pedestrian trails directly on Lake Michigan. We recommend renting Divvy Bikes, which are accessible on almost every block, and exploring a few miles of the trail. If the weather is cooperative, stop at one of Chicago's several beaches while on the trail, walk around Navy Pier and/or visit the Adler Planetarium.
Millennium Park
A touristy attraction, but well worth going to take a selfie if you have never been to Chicago. We recommend a drink at Cindy's Rooftop after your visit, across from the park on Michigan Avenue.
Chicago River Boat Architecture Tours
A must-see if you have never been to Chicago. Any of the tour companies will offer a great experience.
The Second City
National icon for improv comedy shows. We recommend the "Best of the Second City" Show.
The Art Institute of Chicago
One of the best museums in the country.
Wrigley Field
One of the iconic baseball stadiums in America. Even if you don't go to a game, walking around Wrigleyville is awesome.
City Winery at the Chicago Riverwalk
Grab a glass of rose on Chicago's Riverwalk.
Pequod's Pizza
Our favorite Chicago deep dish pizza.
Portillo's Hot Dogs
The only choice for Chicago hot dogs and Italian Beef Sandwiches.
Time Out Market Chicago
The best food hall in Chicago, Time Out Market contains outposts from many of Chicago's best restaurants.
Eataly Chicago
Disneyland for Italian food.
The J. Parker
Relaxed rooftop bar with amazing views of Lake Michigan and Lincoln Park.
Ace Hotel Chicago
One of our favorite rooftop bars in the city with a great view of the skyline.
Kaiser Tiger
Great outdoor beer garden with bocce ball. Plus a beautiful cat lives at the bar (we love him).
Sheffield's Wine & Beer Garden
Great beer garden near our house :)
Au Cheval
The best burger in Chicago. Expect a lengthy wait to get a seat.
Devil Dawgs Belmont
Some of the best late night food in Chicago. Multiple locations throughout the city.
The Publican
A fixture of Chicago's restaurant scene.
The Aviary
Unique cocktail bar.
Green Street Smoked Meats
Converted space in the West Loop with great smoked meats, as well as, a coffee bar (Sawada) and incredible Ramen restaurant (High-Five Ramen).
Beatrix
Delicious brunch with many locations in Chicago.