Iwan Ries & Co is one of The 15 Best Places for Cigars in The Loop, Chicago.

1. Iwan Ries & Co

9.0
19 S Wabash Ave 2nd floor (btwn E Madison St & E Monroe St), Chicago, IL
Smoke Shop · The Loop · 17 tips and reviews

Melvin M.Melvin Mcentee: The cigar selection is great, staff is friendly and they have a free smoking room usually with interesting people inside

Jim T.Jim Tholany: Oldest cigar shop in the county. Selection is unbelievable, staff very helpful to suit ur needs

La Palina CigarsLa Palina Cigars: Try a La Palina cigar! Read more.

Jack Schwartz Importer is one of The 15 Best Places for Cigars in The Loop, Chicago.

2. Jack Schwartz Importer

7.9
141 W Jackson Blvd (at LaSalle St), Chicago, IL
Smoke Shop · The Loop · 2 tips and reviews

Brian P.Brian Powers: Make sure you allow enough time to sit down and enjoy a smoke while sharing fish tales and trading tips with the regulars...bring your coffee with you...you've got plenty of time.

MatthewMatthew: Can't say enough about the staff. Always extremely helpful whether looking for something in store or ordering something online or by phone. Definitely a place to check out.

Atwood is one of The 15 Best Places for Cigars in The Loop, Chicago.

3. Atwood

7.5
1 W Washington St (at State), Chicago, IL
New American Restaurant · The Loop · 57 tips and reviews

Rebecca N.Rebecca Noricks: This is a great little breakfast spot inside the Hotel Burnham - my most favorite boutique hotel in Chicago.

Lisa B.Lisa Bankston: Have the Eggs Benedict at the Atwood on a Sunday morning..you might also see a few celebs. Read more.

Julie P.Julie P: Im not a house vodka fan but The bloody Mary is made with house infused jalapeño vodka!! Life changing!

Trattoria No. 10 is one of The 15 Best Places for Cigars in The Loop, Chicago.

4. Trattoria No. 10

10 N Dearborn St (at Madison St.), Chicago, IL
Italian Restaurant · The Loop · 26 tips and reviews

Danny R.Danny Rodgers: Try the Linguini pasta with roasted eggplant, smoked mozzarella, basil and capers... I had it today and it was Great.

Tracy L.Tracy Lynn: I got the squash ravioli, and my husband got the steak. Both were very delicious. Excellent food at a reasonable price.

David S.David Smith: There's no soup on the menu, but ask if they have the minestrone. It's excellent.

Cafecito is one of The 15 Best Places for Cigars in The Loop, Chicago.

5. Cafecito

8.8
26 E Congress Pkwy (at State St), Chicago, IL
Cuban Restaurant · The Loop · 193 tips and reviews

Zuby H.Zuby H: The tilapia criolla is one of my favorites paired with the rice and beans side. Sandwiches are freshly made and affordably priced for downtown. Can't go wrong.

Bryan A.Bryan Arturo: Wifi pass is cubano01

Time Out ChicagoTime Out Chicago: This Cubano is delicious, and the key to its success is the citrus-garlic-marinated, cumin-rubbed lechon asado and the perfect toasting (whoever is operating the plancha needs a raise).

Cafecito is one of The 15 Best Places for Cigars in The Loop, Chicago.

6. Cafecito

8.4
7 N Wells St (Madison), Chicago, IL
Cuban Restaurant · The Loop · 68 tips and reviews

Chicago TribuneChicago Tribune: Cuban spot with good coffee and more than a dozen sandwiches and platters, notably a killer Cubano sandwich. Read more.

Angela L.Angela LoCicero: The Cafe con Leche is amazing, a large is $2.52. Much better coffee and so much cheaper than that other coffee place. :)

Cheryl A.Cheryl Ann: Cortadito was perfect, not too sweet. And the jerk chicken sandwich is seasoned to perfection!

ROOF on theWit is one of The 15 Best Places for Cigars in The Loop, Chicago.

7. ROOF on theWit

7.5
201 N State St (at Lake St), Chicago, IL
Hotel Bar · The Loop · 131 tips and reviews

Donnie Y.Donnie Young: Super awesome cocktails. Go Pear! And the sliders and fries are great.

Time Out ChicagoTime Out Chicago: TheWit Hotel’s swank rooftop lounge sports a specialty cocktail menu, a well-curated wine list and Mediterranean small plates. Read more.

ThrillistThrillist: The glass-enclosed rooftop offers unparalleled views of the cityscape, as well as a table for four you could probably nab if you got there super early (Protip: get there super early). Read more.

The Palm Chicago is one of The 15 Best Places for Cigars in The Loop, Chicago.

8. The Palm Chicago

7.8
323 E Wacker Dr (at Swissotel), Chicago, IL
Seafood Restaurant · Near East Side · 22 tips and reviews

Adrian W.Adrian Warren: Amazing steaks, seafood, and pastas. Casual yet classy, no reservation required. And don't forget to leave room of desert, all are delicious but big.

Jacob B.Jacob Beckley: Check in here enough and you'll become the mayor.

Ryan B.Ryan Bennett: Great place for a quick drink and apps with friends. Quiet, exceptional service, great atmosphere, and good food.

Palmer House - A Hilton Hotel is one of The 15 Best Places for Cigars in The Loop, Chicago.

9. Palmer House - A Hilton Hotel

7.7
17 E Monroe St (btwn S State St & S Wabash Ave), Chicago, IL
Hotel · The Loop · 263 tips and reviews

Aaron C.Aaron Cruz: Historic, great architecture. Proms, weddings, you name it, it goes on here. Grab one of their many great drinks in the lounge around the Lockwood Restaurant. Get the Bertha cocktail.

Preston M.Preston McClellan: Check out the beautiful ceiling in the lobby.

Ira S.Ira Serkes: Check out the Peacock Door at Monroe Entrance

theWit Chicago - a DoubleTree by Hilton Hotel is one of The 15 Best Places for Cigars in The Loop, Chicago.

10. theWit Chicago - a DoubleTree by Hilton Hotel

8.3
201 N State St (at Lake St), Chicago, IL
Hotel · The Loop · 84 tips and reviews

Valerie D.Valerie D: Best breakfast in state lake tavern. Have the salmon Edda Benedict. They smoke the salmon on site.

Lina G.Lina Gonzo: Nice "Charge Points" in the front lobby! They come in really handy! Like! Like! Like!

Michael C.Michael Colasso: Ask for a suite ending in "04", the views are incredible..and the little things like birds chirping in the morning make this hotel so special. OH and the rooftop bar can't be beat. Get Duck Fat Fries.

Kimpton Hotel Allegro is one of The 15 Best Places for Cigars in The Loop, Chicago.

11. Kimpton Hotel Allegro

171 W Randolph St (N Wells St), Chicago, IL
Hotel · The Loop · 113 tips and reviews

Monika G.Monika Gierszewska: How can you not love them: free morning coffee, evening wine, cosy bathrobes, yoga Matt and channel AND $10 'raid the minibar' voucher!

Adrian S.Adrian Segar: Join the Kimpton Intouch guest program (it's free) and you'll get a $10 credit for your room minibar and free internet!

Douglas M.Douglas M.: Put on your Leopard robe in the closet, order room service then creep the hell out of the guy who delivers it..

Filini Restaurant and Bar is one of The 15 Best Places for Cigars in The Loop, Chicago.

12. Filini Restaurant and Bar

6.7
221 N Columbus Dr (Radisson Blu Aqua Hotel), Chicago, IL
Italian Restaurant · Near East Side · 42 tips and reviews

ThrillistThrillist: Order the olive-oil-poached halibut (Brussels sprouts, wild mushrooms, macadamia nuts) before hitting the downstairs bar with its 100-strong wine collection and spicily-sauced meatballs. Read more.

Dave N.Dave Nevill: Bring your big boy credit card.

Brandan O.Brandan Ortega: Beautiful mosaic tile floor. Lights in the tables are a cool touch.

Walgreens is one of The 15 Best Places for Cigars in The Loop, Chicago.

13. Walgreens

7.9
151 N State St, Chicago, IL
Pharmacy · The Loop · 70 tips and reviews

WalgreensWalgreens: Check out the Upmarket Café where our barista is brewing premium coffee, including the exclusive State and Randolph brand. And did we mention the fresh pastries made daily?

WalgreensWalgreens: You have to check out the LOOK Boutique beauty department upstairs... Nail Bar, Eyebrow Bar, and Virtual Makeover ohh my!

WalgreensWalgreens: Check in and take a fro-yo break at Walgreens!

Bockwinkel's is one of The 15 Best Places for Cigars in The Loop, Chicago.

14. Bockwinkel's

7.1
222 N Columbus Dr, Chicago, IL
Grocery Store · The Loop · 24 tips and reviews

Chris H.Chris Harrison: This is a great little city market. The salad bar, the soups and the rotisserie chicken are all great. Plus the staff is friendly and helpful

Elizabeth T.Elizabeth Towle: Bockwinkel's is the best kept secret (for an inexpensive Loop lunch). Grab a $2 off coupon online before you go and get a generous deli sandwich and 12 oz. soup for $4 and change. Amazing. Read more.

tankboytankboy: Terrific sandwiches at a great price. Totally has a neighborhood deli feel and there's always a bunch of people manning the counter so lines move quickly.