50 Chill Out Vacation Destination In Chicago

1. Segway Experience of Chicago

Address: 224 S Michigan Ave #113, Chicago.

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Segway Experience of Chicago Photo

Chicago's premier Segway Tour company is here to provide you with a fun way to tour the city.

2. Chicago Casino & Poker Rentals

Address: 27 N Upper Wacker Dr Suite 248, Chicago.

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Chicago Casino & Poker Rentals Photo

It provides an unforgettable casino party experience for you and your guests. 

3. Illinois Terminal Operator

Address: 1147 W Ohio St, Chicago.

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Illinois Terminal Operator Photo

This is a casino in Chicago.

4. Sluggers World Class Sports Bar

Address: 3540 N Clark St, Chicago.

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Sluggers World Class Sports Bar Photo

Sports bar with second floor batting cages, skeeball & other games, along with a dueling piano bar.

5. Cook Au Vin

Address: 2256 N Elston Ave, Chicago.

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Cook Au Vin Photo

It provides full -service catering solutions in the Chicago area, from intimate sit-down dinners to large banquet parties. 

6. The Empty Bottle

Address: 1035 N Western Ave, Chicago.

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The Empty Bottle Photo

Indie music venue & bar hosting alternative bands in a somewhat small space with cheap drinks.

7. Subterranean

Address: 2011 W North Ave, Chicago.

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Subterranean Photo

Two-floor venue with a variety of live entertainment from musicians to DJs to burlesque dancers.

8. Lincoln Hall

Address: 2424 N Lincoln Ave, Chicago.

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Lincoln Hall Photo

Midsize live music venue with an on-site restaurant & bar.

9. Bottom Lounge

Address: 1375 W Lake St, Chicago.

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Bottom Lounge Photo

Venue for underground music, beer & casual American comfort food.

10. Thalia Hall

Address: 1807 S Allport St, Chicago.

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Thalia Hall Photo

This landmark venue, designed as an opera house in 1892, hosts concerts by well-known musical acts.

11. Joe's on Weed St.

Address: 940 W Weed St, Chicago.

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Joe's on Weed St. Photo

Big, warehouse-like space to catch a concert or watch the game. 21 & older only.

12. Andy's Jazz Club & Restaurant

Address: 11 E Hubbard St, Chicago.

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Andy's Jazz Club & Restaurant Photo

Live jazz (with admission charge) happens 7 nights a week at this intimate lounge offering dinner.

13. Tiba Restaurant Chicago

Address: 2721 W Lawrence Ave, Chicago.

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Tiba Restaurant Chicago Photo

Unfussy, bare-bones eatery serving an array of Mediterranean dishes such as salads & kebabs.

14. Greek Islands

Address: 200 S Halsted St, Chicago.

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Greek Islands Photo

Since 1971, this eatery has been serving classic Greek dishes in a traditionally decorated space.

15. Reclaimed Bar and Restaurant

Address: 3655 N Western Ave, Chicago.

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Reclaimed Bar and Restaurant Photo

Chill spot serving Southern-accented American eats with craft cocktails amid reclaimed materials.

16. Shibam Restaurant - North

Address: 4807 N Elston Ave, Chicago.

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Shibam Restaurant - North Photo

Relaxed eatery serving classic Yemeni dishes in a casual, colorful space with table & floor seats.

17. Carmine's

Address: 1043 N Rush St, Chicago.

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Carmine's Photo

Lively supper club, famous for its hearty portions of pasta, meat plates & other Italian dishes.

18. Exchequer Restaurant & Pub

Address: 226 S Wabash Ave, Chicago.

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Exchequer Restaurant & Pub Photo

Decades-old pub with pizza, ribs, burgers & other American grub plus a large beer selection.

19. Drawl Southern Cookhouse & Whiskey Room

Address: 2423 N Clark St, Chicago.

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Drawl Southern Cookhouse & Whiskey Room Photo

Chic spot for updated, seasonal Southern cooking & plenty of whiskey in a cozy tasting room.

20. Green Street Smoked Meats

Address: 112 N Green St, Chicago.

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Green Street Smoked Meats Photo

Hip counter serve dishing house-smoked Texas BBQ & homey sides in woodsy, warehouselike digs.

21. Frontier

Address: 1072 N Milwaukee Ave, Chicago.

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Frontier Photo

Game, oysters & tap brews are served in a stylish lodge space with TVs, a fireplace & a beer garden.

22. Beatnik

Address: 1604 W Chicago Ave, Chicago.

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Beatnik Photo

A posh space filled with globe-trotting decor is the setting for New American fare & cocktails.

23. Eddie V's Prime Seafood

Address: 521 N Rush St, Chicago.

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Eddie V's Prime Seafood Photo

Elegant fine-dining chain with a seafood & steak menu, plus a cocktail lounge featuring live jazz.

24. The Capital Grille

Address: 633 N St Clair St, Chicago.

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The Capital Grille Photo

It serves dry-aged steaks and world-class wines.

25. The Berghoff Restaurant

Address: 17 W Adams St, Chicago.

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The Berghoff Restaurant Photo

Institution since 1898 serving traditional German cuisine & steins of beer in an old-world setting.

26. Forastero Restaurant

Address: 449 W North Ave, Chicago.

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Forastero Restaurant Photo

Creative takes on Korean & Mexican dishes, from tacos to rice bowls, in a modern cafe setting.

27. Water Tower Place

Address: 835 N Michigan Ave, Chicago.

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Water Tower Place Photo

Water Tower Place is a large urban, mixed-use development comprising a 758,000 sq ft shopping mall, hotel, theater, and condominiums in a 9 story skyscraper in Chicago, Illinois, United States. The mall is located at 835 North Michigan Avenue, along the Magnificent Mile.

28. 900 North Michigan Shops

Address: 900 Michigan Avenue, Chicago.

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900 North Michigan Shops Photo

900 North Michigan in Chicago, in the U.S. state of Illinois, is a skyscraper completed in 1989. At 871 feet tall, it is currently the ninth-tallest building in Chicago and the 31st-tallest in the United States.

29. The Shops at North Bridge

Address: 520 N Michigan Ave, Chicago.

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The Shops at North Bridge Photo

A mix of stores (clothing, jewelry, cosmetics) shares space with a food court & popular restaurants.

30. Block 37

Address: 108 N State St, Chicago.

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Block 37 Photo

108 North State Street, also known as Block 37, is a development located in the Loop community area of downtown Chicago, Illinois.

31. Diversey Halsted Shopping Center

Address: 740 W Diversey Pkwy, Chicago.

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Diversey Halsted Shopping Center Photo

This is a shopping mall with branded stores, cafes, boutiques, restaurants, etc.

32. Roosevelt Collection Shops

Address: 150 West Roosevelt Road, Chicago.

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Roosevelt Collection Shops Photo

Modern open-air mall with popular chain retailers, a movie theater & a park with a playground.

33. Super Mall

Address: 4222, 5220 S Pulaski Rd, Chicago.

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Super Mall Photo

Indoor marketplace with vendors selling clothing, crafts & unique items, plus casual dining areas.

34. Garrett Popcorn Shops

Address: 27 W Jackson Blvd, Chicago.

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Garrett Popcorn Shops Photo

Garrett Popcorn Shops is dedicated to handcrafting only the finest, gourmet Popcorn

35. SABA Italian Bar + Kitchen

Address: 2715 N Milwaukee Ave, Chicago.

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SABA Italian Bar + Kitchen Photo

Modern Italian cuisine & cocktails are dished out in a stylish setting with ample living greenery.

36. Alinea

Address: 1723 N Halsted St, Chicago.

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Alinea Photo

Chef Grant Achatz draws foodies with New American tasting menus featuring highly creative plates.

37. Heritage Restaurant & Caviar Bar

Address: 2700 W Chicago Ave, Chicago.

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Heritage Restaurant & Caviar Bar Photo

Caviar & vodka are highlighted at this chic Eastern European spot serving breakfast, lunch & dinner.

38. Coffee Slasticarna Drina

Address: 2501 W Lawrence Ave #1f, Chicago.

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Coffee Slasticarna Drina Photo

Bright, modest option for coffee drinks alongside grilled Bosnian fare, pies & baked specials.

39. The Gage

Address: 24 S Michigan Ave, Chicago.

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The Gage Photo

Inventive American eats plus a long list of beers in a lively space with Millennium Park views.

40. Quartino Ristorante

Address: 626 N State St, Chicago.

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Quartino Ristorante Photo

Bustling, bi-level space where groups go for small & large plates plus cocktails & carafes of wine.

41. True Food Kitchen

Address: River North |, 1 W Erie St, Chicago.

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True Food Kitchen Photo

Relaxed, an eco-chic chain serving health-conscious fare, including vegan options, plus cocktails.

42. Next

Address: 953 W Fulton Market, Chicago.

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Next Photo

High-end foodie destination known for Grant Achatz's themed tasting menus & inventive presentations.

43. Weber Grill

Address: 539 N State St, Chicago.

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Weber Grill Photo

Chefs char steaks, burgers, ribs & more on giant Weber kettles in an exhibition-style kitchen.

44. NoMi Kitchen

Address: 800 N Michigan Ave, Chicago.

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NoMi Kitchen Photo

Inside the Park Hyatt, this elegant spot with an outdoor garden serves inventive New American food.

45. Boka

Address: 1729 N Halsted St, Chicago.

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Boka Photo

Creative American cuisine in a stylish, modern setting with a lounge & candelit back garden patio.

46. EL ideas

Address: 2419 W 14th St, Chicago.

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EL ideas Photo

Upscale, intimate BYOB restaurant serving fixed-price American menus in chef Phillip Foss’ kitchen.

47. Smoque BBQ

Address: 3800 N Pulaski Rd, Chicago.

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Smoque BBQ Photo

This BBQ offers classic American cuisines and quick bites.

48. The Purple Pig

Address: 444 Michigan Ave, Chicago.

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The Purple Pig Photo

Expanded outpost of a famed pork & wine specialist with an open kitchen & a chic, airy setting.

49. Tanta Chicago

Address: 118 W Grand Ave, Chicago.

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Tanta Chicago Photo

Inventive Peruvian fare served in a stylish Peru-inspired space; known for its pisco sour cocktail.

50. Sepia

Address: 123 N Jefferson St, Chicago.

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Sepia Photo

Seasonal, inventive, upscale American in brick, tile & wood interior evoking classic Chicago.