Intelligentsia Coffee is one of The 15 Best Pretentious Places in Chicago.

1. Intelligentsia Coffee

9.1
53 E Randolph St (btwn Wabash Ave & Garland Ct), Chicago, IL
Coffee Shop · The Loop · 316 tips and reviews

Audrey T.Audrey Tolbert: Looks pretentious, tastes delicious. Definitely the best coffee in Chicago.

Sam S.Sam Svita: Amazing coffee, great service. A bit overpriced and pretentious though. We already love your coffee, you have nothing to prove...

Lenny L.Lenny Lesser: Best coffee. Some staff might be hipster pretentious.

The Violet Hour is one of The 15 Best Pretentious Places in Chicago.

2. The Violet Hour

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

Time Out ChicagoTime Out Chicago: It's pristine (the carefully constructed cocktails are excellent), pretentious (you won’t find a sign on the door–just look for the long lines) and, ultimately, completely and unarguably gorgeous.

Time Out ChicagoTime Out Chicago: It's pristine (the carefully constructed cocktails are excellent), pretentious (you won’t find a sign on the door–just look for the long lines) and, ultimately, completely and unarguably gorgeous. Read more.

Ross G.Ross Garner: Worth the wait. Unmatched cocktails served in an intimate atmosphere. Go during the week to avoid the long weekend lines.

57th Street Books is one of The 15 Best Pretentious Places in Chicago.

3. 57th Street Books

9.1
1101 E 57th St (at S Kimbark Ave), Chicago, IL
Bookstore · Hyde Park · 16 tips and reviews

Paul L.Paul Luning: This is why you go to an independent bookstore - helpful, enthusiastic, knowledgeable staff that can give good recommendations without being pretentious. Nice layout lends itself to browsing.

Michelin Travel & LifestyleMichelin Travel & Lifestyle: The helpful staff here encourage browsing, and kids can play with toys set out for them in the excellent children's section. -- Green Guide Editor

Explore ChicagoExplore Chicago: A Michelle Obama favorite, this 26-year-old bookstore, part of the Seminary Co-op Bookstores, Inc., is a visually colorful nook with a vast collection children’s and cook books

Pleasant House Pub is one of The 15 Best Pretentious Places in Chicago.

4. Pleasant House Pub

8.7
2119 S Halsted St, Chicago, IL
Pub · East Pilsen · 14 tips and reviews

Lauren T.Lauren Thomas: Scotch egg was delicious, chips were okay. Sticky toffee pudding was also just okay. Vibe was a bit pretentious for calling themselves a "pub" but not a bad evening.

It's A Major PlusIt's A Major Plus: Delicious Royal Pies, incredible baked goods, a great beer list and excellent coffee. Hard to go wrong. Steak & Ale is undeniably satisfying. Chicken Balti is too. Take a fresh loaf of bread with you.

Vithida S.Vithida Sueblinvong: Any kind of pies will do.I have tried beef, chicken and not mushroom and kale, all were delish and of course crunchy scotch egg

Puerto Rico Food and Liquors is one of The 15 Best Pretentious Places in Chicago.

5. Puerto Rico Food and Liquors

8.9
2559 W Augusta Blvd, Chicago, IL
Deli · Humboldt Park · 20 tips and reviews

s.s.: This placed is packed with hard to find micro and craft beer goodies. Its like a specialty shop without all the pretentiousness.. Very knowledgable and always willing to special order. BUY BOOZE HERE!

Shannon J.Shannon Jendrycki: Awesome selection. Awesome people. Fun environment. Awesome selection of odd beers

Dan C.Dan C: Junior takes care of his customers! Best curated beer selection around these parts.

Soho House is one of The 15 Best Pretentious Places in Chicago.

6. Soho House

9.3
113-125 N Green St (at W Randolph St), Chicago, IL
Hotel · West Town · 38 tips and reviews

VODA M.VODA Magazine: The Pizza at Pizza East is excellent. San Daniele, Mozzarella, Arugula, and Parmigiano on a light crispy crust is a winner.

Paul M.Paul Marobella: Atmosphere, food

David S.David Smith: Relax by the pool and check out the view.

Dance Center Chicago is one of The 15 Best Pretentious Places in Chicago.

7. Dance Center Chicago

8.4
3868 N Lincoln Ave, Chicago, IL
Dance Studio · North Center · 3 tips and reviews

Adam C.Adam Clark: Awesome space to learn how to dance in many styles. The drop-in class is friendly and non pretentious. You should go!

Suzanne K.Suzanne Ko: One of the best dance studios for ballroom dance! Take a group lesson, private lesson and wedding dance instruction.

Abir G.Abir Gur: Ryan is a great swing I instructor! Very funny and fun

Starbucks is one of The 15 Best Pretentious Places in Chicago.

8. Starbucks

8.3
1730 W Fullerton Ave, Chicago, IL
Coffee Shop · North Side · 11 tips and reviews

John M.John Mickens: Why not just brew your own coffee, you pretentious cabrons?

GenoGeno: Cool partners. Free parking.....rare find in the city :)

Natasha N.Natasha Nicole: Staff is excellent here!!

Acanto is one of The 15 Best Pretentious Places in Chicago.

9. Acanto

7.9
18 S Michigan Ave, Chicago, IL
Italian Restaurant · The Loop · 27 tips and reviews

Raed M.Raed Mansour: Unbelievably pretentious. Seriously overpriced, small and seems more like a Loop businessman's dating spot after work. Thankfully had one drink and moved on.

Kevin M.Kevin M. McNally, CMP: Simply shared, tasty food offerings at a value price and served via a friendly staff. You must try the Risotto; the flavor cooked perfectly. Applause-Applause for this restaurant.

Chicago TribuneChicago Tribune: You can enjoy budget-friendly pizzas here, as well as some house made pastas. Try the toothsome duck egg spaghetti with creamy pork sugo and grated caciocavallo cheese, a sinfully rich indulgence. Read more.

Hannah's Bretzel is one of The 15 Best Pretentious Places in Chicago.

10. Hannah's Bretzel

8.5
400 N La Salle Dr (at W Kinzie St), Chicago, IL
Sandwich Spot · River North · 43 tips and reviews

Joe H.Joe Hendele: Unbelievably pretentious (it's actually laughable)

bauhausblackbauhausblack: Sergio's Special is yum! Sliced ham, mango sauce & avocado on pretzel bread.

SarahSarah: Sergio Special is the way to go! Delish!!!

Goosefoot is one of The 15 Best Pretentious Places in Chicago.

11. Goosefoot

8.5
2656 W Lawrence Ave (at Washtenaw), Chicago, IL
New American Restaurant · Ravenswood · 25 tips and reviews

AFAR MediaAFAR Media: Beat out every single restaurant in Chicago in 2012 for 'Restaurant of the Year.' It's the most down-to-earth, least pretentious, BYOB friendly, food place that you will ever eat. Read more.

Chicago magazineChicago magazine: Try the miraculous chestnut soup with white Alba mushrooms and truffle essence and the impeccable Angus beef with goosefoot greens, cumin, shallot jus, and ingenious variations on heirloom carrots.

Time Out ChicagoTime Out Chicago: The chef brings precision to every dish on the eight-course tasting menu, highlights of which include a luxurious chestnut-mushroom soup and a Cinderella pumpkin semifreddo coated in nougatine powder. Read more.

HB Home Bistro is one of The 15 Best Pretentious Places in Chicago.

12. HB Home Bistro

3404 N Halsted St (btwn Roscoe St. & Newport Ave.), Chicago, IL
American Restaurant · Lakeview · 35 tips and reviews

Tracey S.Tracey Swanson: Really excellent and constantly changing menu. Seems like it might be pretentious, but really isn't.

Heather W.Heather Williams: The rainbow trout is FANTASTIC! Try it before the menu changes! The escargot could use a little more garlic, but was good. Also the almond stuffed bacon wrapped dates are great!

James G.James Goeke: Bacon. Wrapped. Almond. Stuffed. Dates.

The Whistler is one of The 15 Best Pretentious Places in Chicago.

13. The Whistler

9.0
2421 N Milwaukee Ave (at W Fullerton Ave), Chicago, IL
Cocktail Bar · Logan Square · 110 tips and reviews

Claire P.Claire Pistek: Great craft cocktails. A little hipster pretentious, but good.

Time Out ChicagoTime Out Chicago: Drink this: Bartender Paul McGee's cocktail list is rad. Try the Old Square: Old Weller bourbon and a touch of apple brandy, vermouth and benedictine. Read more.

Time Out ChicagoTime Out Chicago: Bid a temporary good-bye to bartender Paul McGee, whose last night here is Wednesday, February 1st. Read more.

Billy Sunday is one of The 15 Best Pretentious Places in Chicago.

14. Billy Sunday

8.9
3143 W Logan Blvd (Logan and Kedzie), Chicago, IL
Cocktail Bar · Logan Square · 72 tips and reviews

Amy F.Amy Flanagan: Great cocktails, annoyingly pretentious bartenders.

Jamie J.Jamie Jones: Love the Old Fashion and Fernet & Ginger! Always a great experience!

JessicaJessica: Try their drink simply called 'cocktail'. You'll be glad you did.

Bite Café is one of The 15 Best Pretentious Places in Chicago.

15. Bite Café

1039 N Western Ave (at W Cortez St), Chicago, IL
New American Restaurant · Ukrainian Village · 100 tips and reviews

s.s.: This place USED TO BE great. Now it's become a pretentious, line at the door, for the new Wicker Parkers.. Old BITE ruled, new BITE blows.

Heather D.Heather Dumford: Two words: Pork Hash...best combination of flavors I've had for brunch in Chicago

Time Out ChicagoTime Out Chicago: Try the mashbrown from our 100 Best list: The search for the perfect hash browns ends at Bite, where a patty of skin-on potato mash is always fried to a golden crisp.