Chicago: The Right Way

So many of our readers write us asking, “Help! I’m going to Chicago, where should I go while I’m there!? ” So we asked our friends here at The Interrobang!? and our readers, what’s The Right Way to see Chicago? Here’s our top recommendations, in no particular order.


1.  Mollys Cupcakes.  Obviously.  2535 N. Clark Street, 773.883.7220  Home of the world-famous Cupcake, and all delicious things.  Grab a swing and enjoy the best cupcakes in all of Chicago, and some outstanding cookies, brownies, homemade ice cream and some of the best coffees and coffee drinks we’ve ever had.  And say hi to our good friend Mike while your there. He owns the joint.

2.  The Wiener Circle.  2622 N. Clark Street.  Chicago Style hot dogs located conveniently right down the street from Mollys.  Obviously get them Chicago style.

3.  Hot Dougs.  3324 N. California Avenue.  You’ll have to travel a bit but everyone calls it the best dog in town, and the best fries.

4.  Lou Mitchell’s for breakfast.  565 West Jackson Boulevard.  Open since 1923, it’s literally a part of Chicago history.  Get any of the skillet breakfasts, served right in the pan.  It may look like a greasy spoon– and you can definitely go the high cholesterol route– but you’ll also find fair trade coffee, whole grain toast and kick ass egg white omelets.  Delicious and very Chicago.    Free milk duds if you have to wait in line.

5.  Garrett’s Popcorn.  Various locations.  Outstanding caramel corn fresh out of the …whatever they pop and coat the popcorn in.   Basically it comes out still hot, and there is no substitute for that.  Buttery is pretty great too.

6.  Blackbird.  619 W. Randolph.  (312)715-0708 If you want a nice dinner, using great local fresh ingredients, check out Blackbird.  Since everything is seasonally based here, the menu changes often so just order what looks good to you.  We had an outstanding meal there.

7.  Kuma’s Korner.  2900 West Belmont Avenue.  We’ve heard from enough people to trust that this place has one of the best burgers in town and has become a Chicago institution.  Expect lines.

8.  Gibsons Steak.  Again, it’s as much a part of Chicago as anything.  It’s not a ‘secret’ and it might not even be the absolute best steak in the city.  The menu is basic ‘steakhouse’ fare and the apps are just okay but it’s a damn good steak, and its very Chicago.

9.  Fishbar.  Grab a stool at the counter of this truly unique Lakeview spot, where you can order comfort foods (small plates of fried everything) or go trendier with outstanding sashimi’s, carpaccios and tartares.  The selection is small and based on what’s fresh that day.  Great salads, clams, and oysters too.  Get the salted potatos on the side, a bowl of chowder, and anything else after that.  Don’t miss the changing beer list, picked to match up perfectly with the catches of the day.

10.  Publican.  It’s trendy.  But so what, it’s delicious.  Warning, all the tables are communal, and it tends to get loud.  If you’re not willing to give yourself over to that environment, just go to Gibsons.  But if you want a different kind of experience, with fun and surprising menu choices, This is an outstanding choice. Save room for dessert.


When You’re Done Eating- Or In Between Meals, Do Not Miss:

9.  Millenium Park.  One of the best things to do in Chicago.  Check out the Bean, and all of the other iconic sculptures and fountains.  It’s also a great place to view several of Chicago’s skylines.  The Frank Gehry designed amphitheater is completely unique and beautiful and brilliantly designed.  Try to get there when someone is playing music of any kind. We happened upon an afternoon rehearsal there and it was an amazing experience.  And you’ll also want to check out all of the bridges, gardens, walkways and other features of the park.

10.  The Art Institute of Chicago.  Located adjacent to Millenium Park.  If you like art, Ferris Bueller, or even the board game Masterpiece, you wont want to miss the World Famous Art Institute. Its located right alongside Millenium Park so you can kill those two birds in the same afternoon.

11.  Frank Lloyd Wright Home, Studio and Neighborhood.  This requires heading out of downtown to Oak Park, but if you have the time, and like architecture, its a really interesting side trip.  You get to see and tour the house where he lived and worked, but even more fun is the walking tour through the neighborhood where he designed many homes.  The best part of the neighborhood tour is you get to grab headphones and tour on your own timing.

12.  The Rafaello Hotel.  201 E. Delaware Place.  312.943.5000.  We love a good boutique hotel:  big enough to have privacy, but small enough to have a personal touch.  The prices are reasonable and sometimes even better than reasonable (check for upgrades and deals).   For the price of a small room in a big chain hotel, you can have a suite here, and its worth it.  Rainforest shower, sitting room, work area, and you’re  located right off Michigan Avenue, near the beach, shops, restaurants and the water tower.

13. Wrigley Field.  Chicago’s a great sports town, and seeing any sport there is a great experience but nothing beats a visit to Wrigley Field. Currently hosting its 98th year of major league baseball, it’s as much a part of history as it is a part of Chicago culture.  Catch a game if you can, or a tour if you can’t time your visit with a home game.  But make sure you check out this incredible landmark.



That’s it, for us, but here is a collection of some things our readers sent in on twitter to recommend where to go to do Chicago The Right Way.  Let us know if you love or hate anything mentioned here.


tommyjohnagin kumas corner. Great burgers.
jervember  try avec wine bar – blackbird’s more casual and less costly little brother.
kylestacey  One of my favorite spots in Chicago is the Publican. They specialize in pork, oysters and beer.
ianfrommontreal  Shaw’s Crab Shack is a must for us when we go visit our Cubbies
AndyLets   There is a great place to get pasta two blocks from Molly’s called The Pasta Bowl. It is a great place to go before cupcakes.  also Fado Irish Pub is one of the best places in Chicago to watch a soccer game.
WWIFlyingAce  The Weber Grill is a must. Everytime I’m in Chicago, it’s one of the first stops.  Mother Hubbard’s Sports Bar is another great stop.
BryNaylor  Moto Restaurant on W. Fulton
bwalker_78  pippins tavern on rush street is the perfect bar for a real bar guy. No gay club faggy shit
dougschroeder Millers Pub on Wabash
predators1998  Connie’s Pizza S Archer Ave
beyondtgrave  Henry’s Hotdogs.. its like 10 minutes South of Chicago in Cicero.. best hotdogs in the world!
blakeolt Pompei Pizza W.Taylor St. ,Tempo Cafe (best omelette in the city)6 E.Chestnut St., Rosebud on W.Taylor (Fine Italian)Awsome!
Girl_Hicks Lincoln Park Zoo!
detzvin Wrigleyville Dogs 3737 N Clark by the ballpark, My favorite!
DanTomlin portillos and wrigleyville dogs!!! Also 3 schilling to catch a cubs game w free hot dogs!
Goods77  Chicago Style: Gotta do Gibson’s, I will be there tomorrow.
loganfield Been there twice…..Gino’s East Pizza was awesome. The wait was long, but completely worth it.
DerekWeber The Weber Grill – Great steaks, burgers, etc. All cooked over charcoal grills. Downtown.
Pppforme  alinea, bacinos pizza, and next restaurant.
Parmark22  Marge’s for ribs Half shell for sea food Yakzees for burgers. Gino’s East for pizza.Gibson’s for steak. Enjoyl. Love the show.
ryanvaughan78  you gota mention Frontera Grill, @Rick_Bayless is a master of all things Mexican. Don’t get me started on his mole.
JoelFKnox Wrigley Field, Millenium Park, The James Hotel, Shedd Aquarium, The Drake, @sullyhouse Wrigley Field must be #1 on the list.
jimtbishop  best dive bar: The Inner town Pub. No windows, free pool, and Stella on tap.
hughbond Dell Rhea’s Chicken Basket in Willowbrook 30 min w of Chicago on I-55
ChiSoxFanDan Berghoffs and anywhere BUT Wrigley
jmak81  Kingston Mines.
ehombre  Hey Buddies! try Twin Anchors for ribs, Sinatra ate here, neighborhood bar with ribs that might ruin the other places you go 🙁
AnothaJmoore  “The Beat Kitchen” in Roscoe Village on the North Side. Or “The Lincoln Restaraunt” home of the “John Wilkes Booth!”
dhoppsdrw09  Ed Debevics in Chicago is a must!!!!
mmalloy984  I recommend @ButchMcGuires
mqtdavid  chicago dining and drinks at it’s best the Bedford club
nakedtickboy Paddy Long’s in Lincoln Park, good atmosphere and some good bar food try the deep fried bacon and curry fries. and Goose Island Clybourn, it’s a brew pub in Lincoln Park. Delicious beer and gourmet food
joelorenz13  Pippin’s Tavern on Rush.
JacquesTolbert  Carmine’s Italian steak house 1043 N Rush. Great Itaian food, and a very good steak florentine.


  1. WhatWouldRonnieBDo

    October 7, 2011 at 2:38 pm

    Meze- Great atmosphere and great tapas. Then head to Wicker Park at check out Reckless Records… If you like music that is.

  2. Raymond Humphrey

    October 8, 2011 at 9:19 am

    Pequod’s for some killer pan Pizza and Big Star for the best pork belly taco that’ll ever melt in your mouth.

    • God-Defined

      December 7, 2012 at 11:00 pm

      I’ve been here 10 years and Pequods is my fav, although sometimes it’s nice to go for something classic thin, like Aurelios, or Piece (which is also a brewpub in Wicker Park based off CT style).

  3. alanna erin

    October 8, 2011 at 8:12 pm

    avec is a great restaurant, i go there every time i am in chicago!

  4. Ollie

    October 10, 2011 at 11:12 am

    Rustic House, Next, L2O, GT Fish and Oyster are all magnificent places. The Girl and the Goat is one of the most popular places in the city. Hurry, only a few more weeks until winter……

  5. Ollie

    October 10, 2011 at 1:02 pm

    I love Reckless Records. I am also a big fan of Laurie’s Planet of Sound in Lincoln Square.

  6. Geoff_arnstrom

    October 10, 2011 at 2:47 pm

    blues: one werd: buddy guy’s

  7. FuchuBH

    October 11, 2011 at 12:17 pm

    Del Seoul… Just up the street from Molly’s

  8. D.J. Mahan

    October 11, 2011 at 5:57 pm

    The Publican is a MUST. Favorite restaurant in Chicago. All about pork, oysters, and beer. Also any of the Rick Bayless restaurants.

  9. ReaperG

    October 12, 2011 at 11:03 am

    Grant Achatz’s Alinea — arguably the best restaurant in America, expensive but worth the experience. Also G-FEST, the annual Godzilla fan convention.

  10. Kurt Muller

    October 15, 2011 at 5:31 pm

    SweetWater Tavern and Grill, awesome beer selection just off the river

  11. Kurt Muller

    October 15, 2011 at 5:34 pm

    Rosebud Trattoria for good Italian, always go to Smith & Wollensky’s after 11pm, kitchen still open and you can hassle the umpires after a game, this is where they always end up

  12. Anonymous

    November 18, 2011 at 1:21 pm

    Check out the Michelin Guide for Chicago. Just recently released.

  13. Anonymous

    November 18, 2011 at 5:11 pm

    Do not forget about “Barnaby’s Family Inn.” Located on 134 West Golf Road in Schaumburg (though there are other locations throughout the Northwest Suburbs including one by O’Hare Airport on Touhy.

  14. Jdmast

    December 11, 2011 at 7:33 am

    Gene & Georgetti Steakhouse is awesome

  15. Pushykatstubby

    January 27, 2012 at 11:28 pm

    Greek Town, Halsted Street 4 blocks from the United Center where you can enjoy a Bulls or a Blackhawks game. Leave your wallet at home!

  16. PatInTheBronx

    May 31, 2012 at 1:08 pm

    During the cold weather go to the Madhouse on Madison for a blackhawks game..

  17. TwoNumberOnes

    August 13, 2012 at 7:53 pm

    Went to the Wiener Circle on Saturday. Got a chocolate shake. Well worth it.

  18. tampajim

    September 24, 2012 at 12:20 pm

    Disagree with number 3, Jan and Judes has the best dogs and fries in town, well, a little outside of it (river grove), but if you have to drive to the other, i would much rather drive to this one.

  19. OllieInChicago

    November 15, 2012 at 1:37 pm

    The Christkindlmarket opens November 20 in Daley Plaza.

  20. FezKilledHisCat

    November 17, 2012 at 8:24 am

    I’m a big fan of Portillo’s.  Also, Harry Carey’s is great for steak or Italian entrees.  Another place I used to eat at regularly when I lived in Chicago 20 yrs. ago was called the “Fish Keg”.  It was on the far north side (on Howard Street maybe) near the lake and was across the street from the City of Evanston.  They would fry up whatever fish you requested, with my favorites being Smelt and Rainbow Trout.  If the Fish Keg is still in business, I would highly recommend it if you love good fried fish!

  21. jimmyusa

    December 2, 2012 at 7:23 pm

    One day a month, I make a 3 hour round trip just to have lunch (Coney Island Polish) at a Portillo’s, then buy some Italian Beef to take home for dinner that night. Nuthin better…

  22. God-Defined

    December 7, 2012 at 10:36 pm

    Favorite Wrigleyville bar for a game or for fucking around is Murpheys Bleachers.  Nice large space on a corner lot.  They have a great beer selection that’s always updating, good food, great service. They treat locals like kings, and let you cornhole in the back!   
    Skip the Wrigleyville Goose Island brewpub, and go to the Clybourn location.  The Music Box Theater is a great place to see an old or new movie, just blocks west.  World Bar on Irving Park is great for soccer games.  Mad River on Sheffield has killer burgers, and is a great place to see a football game.  Uncommon Ground Cafe in Wrigley is a great place for a coffee or beer, and at night they usually have great music in the small back room.  Pick Me Up Cafe is open 24 hrs, and has the best Club Sammich I’ve ever had. Shit there’s so much to do.  Risque Cafe is another good bar in the neighborhood.

  23. HackProphet

    September 9, 2013 at 8:53 pm

    New York Bagel and Bialy, though not technically in chicago, is the best bagel I’ve had anywhere.  Jalapeno cream cheese is unbelievable

  24. utterdisgrace

    April 30, 2014 at 4:11 pm

    Crisp on Broadway in Lakeview.  Incredible korean fusion food – some of the best fried chicken in the country.