Escape Guide // Chicago, IL
Hopleaf Bar is one of Escape Guide // Chicago, IL.

1. Hopleaf Bar

9.2
5148 N Clark St (at W Foster Ave), Chicago, IL
Beer Bar · Andersonville · 334 tips and reviews

Hudson SutlerHudson Sutler: This bar has been slingin’ beer for 25 years, and recently added onto the kitchen to satisfy any of your stick-to-your-ribs bar food needs. Read more.

The Map Room is one of Escape Guide // Chicago, IL.

2. The Map Room

8.6
1949 N Hoyne Ave (at W Armitage Ave), Chicago, IL
Beer Bar · Bucktown · 108 tips and reviews

Hudson SutlerHudson Sutler: It’s a casual bar with beer you’ve never heard of and probably could never pronounce. Read more.

The Drifter is one of Escape Guide // Chicago, IL.

3. The Drifter

7.9
678 N Orleans St (Huron), Chicago, IL
Speakeasy · River North · 23 tips and reviews

Hudson SutlerHudson Sutler: It’s dark and it’s eerie inside, & that’s what the owner was going for. The big attraction to this bar is the dark, almost gothic, entertainment which is curated to match the image of the bar. Read more.

Three Dots and a Dash is one of Escape Guide // Chicago, IL.

4. Three Dots and a Dash

8.6
435 N Clark St (btwn Illinois & Hubbard St), Chicago, IL
Tiki Bar · Near North Side · 223 tips and reviews

Hudson SutlerHudson Sutler: It’s a Hawaii themed lounge with awesome cocktails made with fresh fruit juice. The food served is light and tropical. Every city should have a bar like this. Read more.

The Wiener's Circle is one of Escape Guide // Chicago, IL.

5. The Wiener's Circle

7.6
2622 N Clark St (btwn Drummond Pl & Wrightwood Ave), Chicago, IL
Hot Dog Joint · Park West · 130 tips and reviews

Hudson SutlerHudson Sutler: Hot dogs, fries, burgers, you name it, they’ve got it. Famous for berating their customers, you’re sure to end your night with some quality entertainment; especially if you order the Chocolate Shake. Read more.

Superdawg Drive-In is one of Escape Guide // Chicago, IL.

6. Superdawg Drive-In

9.0
6363 N Milwaukee Ave (btwn Devon Ave & Highland Ave), Chicago, IL
Hot Dog Joint · Norwood Park · 162 tips and reviews

Hudson SutlerHudson Sutler: It’s a super casual and classic experience that’s hard to find anymore. Pull up, order, and eat this classic American food. Read more.

Joe's Seafood, Prime Steak & Stone Crab is one of Escape Guide // Chicago, IL.

7. Joe's Seafood, Prime Steak & Stone Crab

9.4
60 E Grand Ave (at N Rush St), Chicago, IL
Seafood Restaurant · Near North Side · 225 tips and reviews

Hudson SutlerHudson Sutler: This is an awesome date spot, one that you’ll thoroughly enjoy too. If you’re having trouble deciding between a steak and seafood, allow us to suggest the fried chicken. Read more.

Portillo's is one of Escape Guide // Chicago, IL.

8. Portillo's

9.0
100 W Ontario St (at Clark St), Chicago, IL
Hot Dog Joint · River North · 667 tips and reviews

Hudson SutlerHudson Sutler: Tough to find outside of Chicago, the highlight here is the Italian Beef Sandwich- part french dip, part New Orleans Muffuletta, all delicious. Read more.

Au Cheval is one of Escape Guide // Chicago, IL.

9. Au Cheval

9.1
800 W Randolph St (at S Halsted St), Chicago, IL
Burger Joint · Fulton Market · 482 tips and reviews

Hudson SutlerHudson Sutler: Self described as a “diner style bar & restaurant with a passion for eggs,” Au Cheval is getting most of their acclaim from their top notch burger which many claim is the best in the country. Read more.

Lou Malnati's Pizzeria is one of Escape Guide // Chicago, IL.

10. Lou Malnati's Pizzeria

8.7
439 N Wells St (btwn Illinois St & Hubbard St), Chicago, IL
Pizzeria · River North · 332 tips and reviews

Hudson SutlerHudson Sutler: There's not much more iconic than Chicago Deep Dish pizza and while everyone has their favorite, for us no one has been doing it better than Lou's. Read more.

Sawada Coffee is one of Escape Guide // Chicago, IL.

11. Sawada Coffee

9.2
112 N Green St, Chicago, IL
Coffee Shop · West Town · 63 tips and reviews

Hudson SutlerHudson Sutler: Did you know there are world renowned baristas? Apparently one of them owns this place and his name is Hiroshi Sawada. This dude makes killer caffeine concoctions for you to enjoy. Read more.

Millennium Park is one of Escape Guide // Chicago, IL.

12. Millennium Park

9.5
201 E Randolph St (btwn Columbus Dr & Michigan Ave), Chicago, IL
Park · Grant Park · 619 tips and reviews

Hudson SutlerHudson Sutler: Millennium Park, maybe better known as the home of that giant reflective thing that looks like a bean. Go and snap a few pics with “The Bean” then head over to Wrigley Square. Read more.

Navy Pier is one of Escape Guide // Chicago, IL.

13. Navy Pier

8.6
600 E Grand Ave (at Streeter Dr), Chicago, IL
Pier · Streeterville · 371 tips and reviews

Hudson SutlerHudson Sutler: Take a boat tour of Lake Michigan. See a play at Chicago Shakespeare Theater. Take a ride on the Centennial Wheel. Navy Pier is the perfect place to kill a few hours between meetings and obligations. Read more.

Burnham Shores Park is one of Escape Guide // Chicago, IL.

14. Burnham Shores Park

1181-1239 Lake Shore Blvd (at Lake Michigan), Evanston, IL
Playground · 3 tips and reviews

Hudson SutlerHudson Sutler: Burnham Park is a great place to go if you’re looking for some r&r. There’s an awesome lakefront beach that’s slightly outshined by Northerly Island which grants some incredible views of the city. Read more.

State Street is one of Escape Guide // Chicago, IL.

15. State Street

State St, Chicago, IL
Road · The Loop · 1 tip

Hudson SutlerHudson Sutler: State Street is a historic shopping area located in the heart of the Windy City. There’s loads of shops to pick up great clothes & trinkets on State Street. It’s also scattered with art installations. Read more.

The Buckingham Club is one of Escape Guide // Chicago, IL.

16. The Buckingham Club

6.8
440 S La Salle St (Congress), Chicago, IL
Hotel · The Loop · 3 tips and reviews

Hudson SutlerHudson Sutler: If you’re trying to stay in for a night while here, wander down to the Milk Room for a classic cocktail, then hit up the Game Room for a gentlemanly game of bocce ball. Read more.