Chicago longtime favorites
Lakefront Trail is one of Chicago longtime favorites.

1. Lakefront Trail

9.4
Lake Michigan Lakefront (at N Lake Shore Dr), Chicago, IL
Hiking Trail · Grant Park · 132 tips and reviews
Twin Anchors Restaurant & Tavern is one of Chicago longtime favorites.

2. Twin Anchors Restaurant & Tavern

8.9
1655 N Sedgwick St (at Eugenie St), Chicago, IL
BBQ Joint · Old Town Triangle · 89 tips and reviews
Do-Rite Donuts & Coffee is one of Chicago longtime favorites.

3. Do-Rite Donuts & Coffee

50 W Randolph St (at N Dearborn St), Chicago, IL
Donut Shop · The Loop · 112 tips and reviews
Chicago Riverwalk is one of Chicago longtime favorites.

4. Chicago Riverwalk

9.4
Chicago River, Chicago, IL
Waterfront · The Loop · 139 tips and reviews
Portillo's is one of Chicago longtime favorites.

5. Portillo's

9.0
100 W Ontario St (at Clark St), Chicago, IL
Hot Dog Joint · River North · 667 tips and reviews
Del Seoul is one of Chicago longtime favorites.

6. Del Seoul

8.9
2568 N Clark St (at W Wrightwood Ave), Chicago, IL
Korean Restaurant · Park West · 162 tips and reviews
Jay Pritzker Pavilion is one of Chicago longtime favorites.

7. Jay Pritzker Pavilion

9.2
201 E Randolph St (btwn Columbus Dr & Michigan Ave), Chicago, IL
Amphitheater · Grant Park · 101 tips and reviews
Parson's Chicken & Fish is one of Chicago longtime favorites.

8. Parson's Chicken & Fish

9.0
2952 W Armitage Ave (btwn N Humboldt & N Richmond), Chicago, IL
Fried Chicken Joint · Logan Square · 184 tips and reviews
Homeslice is one of Chicago longtime favorites.

9. Homeslice

9.0
938 W Webster Ave (at Bissell St), Chicago, IL
Pizzeria · North Side · 83 tips and reviews
Kingston Mines is one of Chicago longtime favorites.

10. Kingston Mines

9.0
2548 N Halsted St (at Wrightwood Ave), Chicago, IL
Jazz and Blues Venue · Lincoln Park · 110 tips and reviews
Cindy's is one of Chicago longtime favorites.

11. Cindy's

8.6
12 S Michigan Ave (btwn E Madison & E Monroe St), Chicago, IL
New American Restaurant · The Loop · 144 tips and reviews
The Aviary is one of Chicago longtime favorites.

12. The Aviary

8.8
955 W Fulton Market (at Morgan St.), Chicago, IL
Cocktail Bar · Fulton Market · 174 tips and reviews
Scofflaw is one of Chicago longtime favorites.

13. Scofflaw

9.3
3201 W Armitage Ave (at Kedzie Ave), Chicago, IL
Cocktail Bar · Logan Square · 149 tips and reviews
Goose Island Beer Co. is one of Chicago longtime favorites.

14. Goose Island Beer Co.

8.7
1800 W Fulton St (btwn Wolcott Ave & Wood St), Chicago, IL
Brewery · West Town · 30 tips and reviews
North Avenue Beach is one of Chicago longtime favorites.

15. North Avenue Beach

9.0
1600 N Lake Shore Dr (btwn Fullerton Pkwy & North Ave), Chicago, IL
Beach · Lincoln Park · 81 tips and reviews
Bloomingdale Trail — The 606 is one of Chicago longtime favorites.

16. Bloomingdale Trail — The 606

9.2
Bloomingdale Ave, Chicago, IL
Hiking Trail · Bucktown · 26 tips and reviews
The Art Institute of Chicago is one of Chicago longtime favorites.

17. The Art Institute of Chicago

9.5
111 S Michigan Ave (btwn Monroe St & Jackson Dr), Chicago, IL
Art Museum · Grant Park · 685 tips and reviews
Crisp is one of Chicago longtime favorites.

18. Crisp

8.6
2940 N Broadway St (btwn W Oakdale Ave & W Wellington Ave), Chicago, IL
Fried Chicken Joint · Lake View East · 174 tips and reviews
Girl & The Goat is one of Chicago longtime favorites.

19. Girl & The Goat

9.0
809 W Randolph St (at Halsted St), Chicago, IL
New American Restaurant · West Town · 552 tips and reviews
Publican Quality Meats is one of Chicago longtime favorites.

20. Publican Quality Meats

9.4
825 W Fulton Market (at N Green St), Chicago, IL
Deli · Fulton Market · 133 tips and reviews
Small Cheval is one of Chicago longtime favorites.

21. Small Cheval

8.9
1732 N. Milwaukee Ave, Chicago, IL
Burger Joint · Bucktown · 74 tips and reviews
Longman & Eagle is one of Chicago longtime favorites.

22. Longman & Eagle

9.2
2657 N Kedzie Ave (at W Schubert Ave), Chicago, IL
New American Restaurant · Logan Square · 352 tips and reviews
Avec is one of Chicago longtime favorites.

23. Avec

9.2
615 W Randolph St (at N Jefferson St), Chicago, IL
New American Restaurant · West Loop · 214 tips and reviews
Piece Brewery and Pizzeria is one of Chicago longtime favorites.

24. Piece Brewery and Pizzeria

9.2
1927 W North Ave (btwn Elk Grove Ave & Damen Ave), Chicago, IL
Pizzeria · Wicker Park · 349 tips and reviews
Lula Café is one of Chicago longtime favorites.

25. Lula Café

9.3
2537 N Kedzie Blvd (btwn Linden & Logan Sq.), Chicago, IL
Café · Logan Square · 256 tips and reviews
90 Miles Cuban Cafe is one of Chicago longtime favorites.

26. 90 Miles Cuban Cafe

8.8
2540 W Armitage Ave (at Stave St), Chicago, IL
Cuban Restaurant · Logan Square · 173 tips and reviews
Hopleaf Bar is one of Chicago longtime favorites.

27. Hopleaf Bar

9.2
5148 N Clark St (at W Foster Ave), Chicago, IL
Beer Bar · Andersonville · 334 tips and reviews
Big Star is one of Chicago longtime favorites.

28. Big Star

8.9
1531 N Damen Ave (at N Wicker Park Ave), Chicago, IL
Taco Restaurant · Wicker Park · 571 tips and reviews