Chicago's Greatest Hits
Clarence Buckingham Memorial Fountain is one of Chicago's Greatest Hits.

1. Clarence Buckingham Memorial Fountain

9.1
301 S Columbus Dr (btwn Jackson Dr & Balbo Dr), Chicago, IL
Fountain · Grant Park · 133 tips and reviews

Jake S.Jake Smith: The fountain represents Lake Michigan, with each sea horse pair symbolizing the states of Illinois, Wisconsin, Michigan and Indiana, that border the lake.

Delilah's is one of Chicago's Greatest Hits.

2. Delilah's

8.9
2771 N Lincoln Ave (at W Diversey Pkwy), Chicago, IL
Whisky Bar · North Side · 106 tips and reviews

Jake S.Jake Smith: Drink some Maker's Mark; rumor has it the neon sign out front was custom made by Maker's and given to the bar because they sold such a high volume of the Bourbon brand.

Galway Bay is one of Chicago's Greatest Hits.

3. Galway Bay

7.2
500 W Diversey Pkwy (at N. Pine Grove Ave.), Chicago, IL
Pub · Lake View East · 25 tips and reviews

Jake S.Jake Smith: They have an extensive video game collection. I highly recommend browsing through it before ultimately deciding upon playing drunken "Goldeneye" with friends.

Green Mill Cocktail Lounge is one of Chicago's Greatest Hits.

4. Green Mill Cocktail Lounge

8.7
4802 N Broadway St (at W Lawrence Ave), Chicago, IL
Jazz and Blues Venue · Uptown · 133 tips and reviews

Jake S.Jake Smith: In Michael Mann's "Thief" (1981), the title character (played by James Caan) owns the Green Mill. Go rent it to see what happens to the bar at the climax of the film.

Au Cheval is one of Chicago's Greatest Hits.

5. Au Cheval

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

Jake S.Jake Smith: I am amazed at how something as familiar as a burger and fries can become such a new experience to me. It happens at Au Cheval.

Kuma's Corner is one of Chicago's Greatest Hits.

6. Kuma's Corner

8.8
2900 W Belmont Ave (at Francisco Ave), Chicago, IL
Burger Joint · Northwest Side · 417 tips and reviews

Jake S.Jake Smith: Not only did they name a burger after the greatest band of all-time, its toppings are exactly what I love on a burger (pulled pork, bacon, cheddar, pickles). Order a Led Zeppelin and a grape soda.

The Violet Hour is one of Chicago's Greatest Hits.

7. The Violet Hour

8.9
1520 N Damen Ave (at Pierce Ave), Chicago, IL
Speakeasy · Wicker Park · 255 tips and reviews

Jake S.Jake Smith: Please, follow the house rules. Please.

Wrigley Field is one of Chicago's Greatest Hits.

8. Wrigley Field

9.0
1060 W Addison St (btwn Sheffield Ave & Clark St), Chicago, IL
Baseball Stadium · Wrigleyville · 562 tips and reviews

Jake S.Jake Smith: Get up in the middle of the 7th and sing your heart out during "Take Me Out to the Ballgame" with whichever celeb is leading the song.

The Berghoff Restaurant is one of Chicago's Greatest Hits.

9. The Berghoff Restaurant

8.1
17 W Adams St (btwn S Dearborn St & S State St), Chicago, IL
German Restaurant · The Loop · 150 tips and reviews

Jake S.Jake Smith: The perogie appetizer is excellent and goes well with the free root beer you get for checking in.

Bobtail Ice Cream Company is one of Chicago's Greatest Hits.

10. Bobtail Ice Cream Company

2951 N Broadway St (at W Wellington Ave), Chicago, IL
Ice Cream Parlor · Lake View East · 86 tips and reviews

Jake S.Jake Smith: Whichever flavor you choose, get an Oreo dipped waffle cone with it.

Smoque BBQ is one of Chicago's Greatest Hits.

11. Smoque BBQ

9.1
3800 N Pulaski Rd (at Grace St), Chicago, IL
BBQ Joint · Old Irving Park · 232 tips and reviews

Jake S.Jake Smith: A pulled pork sandwich truly done right - huge hunks of meat on a delicious bun. A nearly perfect sauce. Points deducted for the coleslaw though, it's more like an onion salad.

Oz Park is one of Chicago's Greatest Hits.

12. Oz Park

8.9
2021 N Burling St (btwn Webster Ave & Dickens Ave), Chicago, IL
Park · Lincoln Park · 29 tips and reviews

Jake S.Jake Smith: This park is named after the magical land of Oz, created by L. Frank Baum. The children's author was a Lincoln Park resident in the 1890s.

The Field Museum is one of Chicago's Greatest Hits.

13. The Field Museum

9.0
1400 S Lake Shore Dr (at McFetridge Dr), Chicago, IL
History Museum · Museum Campus · 357 tips and reviews

Jake S.Jake Smith: Check out the engraved diamond pin in the gem exhibit. It has the Dutch king's face on it!

Pequod's Pizzeria is one of Chicago's Greatest Hits.

14. Pequod's Pizzeria

8.9
2207 N Clybourn Ave (btwn W Webster Ave & N Greenview Ave), Chicago, IL
Pizzeria · North Side · 297 tips and reviews

Jake S.Jake Smith: Order a deep dish pizza (with sausage!) to go. Order cheesy bread and a beer while you wait.

Gino's East is one of Chicago's Greatest Hits.

15. Gino's East

8.1
162 E Superior St (btwn Fairbanks Ct & Michigan Ave), Chicago, IL
Pizzeria · Streeterville · 272 tips and reviews

Nick R.Nick Ross: Place is amazing. Get the meaty legend!

Oak Street Beach is one of Chicago's Greatest Hits.

16. Oak Street Beach

9.1
1000 N Lake Shore Dr (at Oak St), Chicago, IL
Beach · Gold Coast · 57 tips and reviews

Jake S.Jake Smith: Head to the Magnificent Mile for lunch or dinner after a day at the beach; it's literally less than a hundred paces away.

Music Box Theatre is one of Chicago's Greatest Hits.

17. Music Box Theatre

9.4
3733 N Southport Ave (btwn Grace St & Waveland Ave), Chicago, IL
Indie Movie Theater · Lakeview · 88 tips and reviews

Jake S.Jake Smith: If the movie you're seeing calls for audience participation, participate! The staff sometimes hands out sheets with information about how you can participate better during the film.

18. Logan Hardware

2532 W Fullerton Ave (at N Western Ave), Chicago, IL
Record Store · Logan Square · 21 tips and reviews

Jake S.Jake Smith: Bring $10.00 (at least) for records, but leave your quarters at home.

Lincoln Park Zoo is one of Chicago's Greatest Hits.

19. Lincoln Park Zoo

9.1
2001 N Clark St (btwn Fullerton Pkwy & LaSalle Dr), Chicago, IL
Zoo · Lincoln Park · 283 tips and reviews

Jake S.Jake Smith: They filmed the zoo scenes in Baby's Day Out here (the gorilla cage scene was actually in the cat house).

Alice's Lounge is one of Chicago's Greatest Hits.

20. Alice's Lounge

6.9
3556 W Belmont Ave (at N Central Park Ave), Chicago, IL
Karaoke Bar · Northwest Side · 17 tips and reviews

Jake S.Jake Smith: There are no "numbers" or "codes" for songs to write down, so if you know your song, simply find a slip and jot it down with your first name and last initial.

The Second City is one of Chicago's Greatest Hits.

21. The Second City

9.2
1616 N Wells St (btwn Concord Ln & North Ave), Chicago, IL
Comedy Club · Old Town Triangle · 151 tips and reviews
Chicago Architecture Center River Cruise is one of Chicago's Greatest Hits.

22. Chicago Architecture Center River Cruise

9.4
112 E Wacker Dr (at Michigan Ave), Chicago, IL
Tour Provider · The Loop · 106 tips and reviews
The Redhead Piano Bar is one of Chicago's Greatest Hits.

23. The Redhead Piano Bar

6.5
16 W Ontario St, Chicago, IL
Piano Bar · Near North Side · 61 tips and reviews

Jake S.Jake Smith: Try the Cougartini.

Sluggers World Class Sports Bar and Grill is one of Chicago's Greatest Hits.

24. Sluggers World Class Sports Bar and Grill

7.1
3540 N Clark St (at Eddy St), Chicago, IL
Sports Bar · Wrigleyville · 85 tips and reviews

Jake S.Jake Smith: This place is huge. If the front bar is crowded, the back bar/upstairs/patio are most likely empty. Make your way there to get your beers instead of waiting.

Big Star is one of Chicago's Greatest Hits.

25. Big Star

9.0
1531 N Damen Ave (at N Wicker Park Ave), Chicago, IL
Taco Restaurant · Wicker Park · 571 tips and reviews

Jake S.Jake Smith: Sonoran hot dog, with any of their surprisingly refreshing whiskey drinks, while sitting at the bar is the way to go.

The Signature Lounge at the 96th is one of Chicago's Greatest Hits.

26. The Signature Lounge at the 96th

7.4
875 N Michigan Ave (btwn Delaware Pl & Chestnut St), Chicago, IL
Lounge · Streeterville · 307 tips and reviews

Jake S.Jake Smith: Don't be fooled. The north side views are just as good as the sought-after south and east side views.

Tribune Tower is one of Chicago's Greatest Hits.

27. Tribune Tower

435 N Michigan Ave (at E Illinois St), Chicago, IL
Structure · Streeterville · 57 tips and reviews

Jake S.Jake Smith: Find the rock from the state (or perhaps country) you're visiting from.

Chicago Q is one of Chicago's Greatest Hits.

28. Chicago Q

8.5
1160 N Dearborn St (at W Division St.), Chicago, IL
BBQ Joint · Near North Side · 167 tips and reviews

Jake S.Jake Smith: The Pulled Pork sandwich is delectable and "The Q" uses the PERFECT bun. Try it with the South Carolina Mustard sauce; I couldn't get enough. Is this the best Pulled Pork in Chicago? It might be.