I've been very open about my travels to and from Chicago over the past three or four years — and obviously my move here last autumn. I get so many emails and messages from readers asking me what they should do and check out while they're here. It's a bit overwhelming at times, because I want to recommend everything. I love my city. So, finally, I give you this: Mini Penny's favorite Chicago spots. If you have anything you'd like to add, feel free to pop it in the comments! Hopefully this will be a list that grows and changes over the years. Enjoy!
Check 'em out after the jump. (Updated Winter 2015)
Food
Cemitas Puebla (3619 West North Ave, 817 West Fulton Market)
This is hands-down my favorite food on the planet. My friend Beau introduced me to this otherwise unnoticed location and it might be one of the best things anyone has ever done for me. For meat eaters (as I used to be), the carne asada sandwich is out of this world. For vegetarians, the veggie cemita is to die for. Their guacamole is smooth and delicious, the horchata is perfect, and the family-owned atmosphere is comforting and full of culture. Recently, they opened a second location in the West Loop. This is a don't miss. I'm serious.
The Chicago Diner (3411 North Halsted, 2333 North Milwaukee Ave)
Vegans rejoice and get yourself a dairy-free milkshake.
Pequod's Pizza (2207 North Clyborn)
I'm not a fan of Chicago-style pizza. But if you HAVE to do it, go to Pequod's. Note: there's a bad painting of Gandalf in the men's restroom.
Black Dog Gelato (1955 W Belmont, 859 N Damen Ave)
Skip Jeni' and go to Black Dog. They're local and have far better flavors.
Kuma's Corner (2900 West Belmont, 666 W. Diversey)
The only excuse not to go here is if you're vegan (unfortunately they have no vegan options). It's a metal-themed burger joint with the most interesting and delicious combinations. Their veggie burgers are amazing! Tip: Don't go on a weekend, and go early. The wait is normally a while. I opt to eat at the bar for faster serving.
Molly's Cupcakes (2536 North Clark Street)
Red Velvet. Banana. Peach Cobbler. Pumpkin. Cupcakes. Need I say more? Oh, and they also have vegan options.
Sultan's Market (Various Locations)
This little spot has great falafel and shawarma (for you meat eaters). I love picking up Coca-Cola here because the bottles are in Arabic! Tip: Cash only!
Dimo's Pizza (Various locations)
They have great normal pizza — thin crust — with a variety of awesome topping combinations. From vegan nacho to mac and cheese, they've got it.
Bang Bang Pie Shop (2051 North California)
They have so much amazing pie at this place, it's insane. And their biscuits? Don't even get me started. Tip for vegans: they use lard in some of their pie crusts, so be sure to ask!
Whisk (2018 West Chicago)
Check out Whisk for brunch. Their selection of Benedict is rad and they have a killer soda list. My personal favorite is the almond cola!
HASH (1357 North Western Ave)
Everything is a potato-based dish — i.e., different versions of hash browns. I love coming here for brunch.
Soup Box (2943 North Broadway, 50 East Chicago)
Soup Box is my winter-time pick me up. They have twelve different types of soup each day, along with grilled cheese and bread. Simple and to the point and super tasty.
Swedish Bakery (5348 North Clark)
They have marzipan frogs and plenty of other great treats. I am a sucker for the various kinds of butter cookies. Andersonville is a great neighborhood to walk around in, I highly recommend it.
Big & Little's (1034 West Belmont)
The Ahi Tuna Taco is my standard work dinner. It's so good and is one of lighter sides of their menu.
Goddess and the Grocer (Various)
I normally go to Goddess in Bucktown. It's a great small grocery store with sandwich, soup, and other hot bar items. Their chicken salad sandwich is so damn good and there are so many good eats that it can sometimes be hard to choose!
Dove's Luncheonette (1545 North Damen)
This is a newer spot that opened in Wicker Park. They have a limited menu, but everything on it is fantastic. After you're done with your food, you can finish with a slice of pie from Hoosier Mama's.
Coffee
Gaslight Coffee Roasters (2385 North Milwaukee)
This is my neighborhood coffee shop!
Asado (Chicago Ave, Irving Park, Pickwick Lane)
My favorite combo is the almond loaf with an Especiales pour over. Great, quiet atmosphere and great design.
The Wormhole (1462 North Milwaukee)
This used to be my favorite coffee shop to visit, but over time has become very touristy. Don't get me wrong, there's a DeLorean and it's decorated with movie memorabilia from my childhood. The drinks are great and it has plenty of cool vibes. Just don't expect to be able to sit and work anywhere. It's great for getting good coffee on the go when you're shopping in Wicker. Not into coffee? Try Rocket Sauce in the summer time!
Buzz: Killer Espresso (1644 North Damen)
If you're in Wicker but don't want to put up with the crowded (and sometimes touristy) nature of Wormhole, but don't want to settle for crappy Caribou or Starbucks, I urge you to go to Buzz. Great coffee and chill vibes. They make a mean dirty chai.
Cafe Streets (1750 West Division)
A really fantastic coffee shop. I typically stay away because an ex-lover works there (oops, way to ruin a coffee shop for myself), but in the summer always manage to wander in for some fresh limeade.
Bars
Slippery Slope (2357 North Milwaukee)
This bar is the answer to Bonny's sudden closing a few years ago. Each night has a different theme, and weekends are an all-out dance party. Come here with the expectation to see people of all different types — hipsters, bros, woo girls, you name it.
Danny's (1951 West Dickens)
They host The Smiths/Morrissey night at the end of each month. That's all you need to know.
Three Aces (1321 West Taylor)
There's a bit of the motorcycle/rockabilly thing going on here (we went on a Sockhop Saturday). We sat at the bar and ordered a pizza that was delish. Again, another killer staff and nice sized patio.
The Orbit Room (2959 North California)
This is another spot that Gedi brought to light for me. It's super close to home and has a nice retro vibe and huge patio. The staff is entertaining and it's just enough off the beaten path to be comforting and doesn't have the try-hard feel of some other places nearby. This is an easy bar to go to just to hang out, have a drink, and a conversation (or even grab some food if you're feeling it!).
Delilah's (2771 North Lincoln)
This is another bar that my friends took me to years ago during one of my visits. It's a nice change from other bars in the area with Punk, Rockabilly, and ska nights.
The Rocking Horse (2535 North Milwaukee, 2363 North Milwaukee)
Do yourself a favor and sit at the bar, chit chat with the friendly bartenders, drink some gin and order the ranch tater tots. There's enough to share.
Revel Room (1566 North Milwaukee)
This is one of the few Wicker Park bars that isn't terrible to be at on the weekends. It's got a great vibe, multiple rooms, and great cocktails.
Emporium Arcade Bar (1366 North Milwaukee)
Both locations have a great beer selection and a huge rooms of arcade games. It's best to hit this place up at non-peak hours and weekdays if you want to get your turn at NBA jam or Twilight Zone pinball.
Headquarters (2833 North Sheffield)
Another great arcade bar in a different part of town — bonus: games are free to play!
Scofflaw (3201 West Armitage)
A gin bar that serves fresh cookies at midnight. Or, if you're a day person, go for brunch and sit by the fireplace.
Sportsman's Club (948 North Western)
This is like if you were to drink in your dad's den... that happened to be inside the Field Museum. Super den-like with taxidermy and low lights. A cool vibe for sure!
Shopping
Myopic Books (1564 North Milwaukee)
This reminds me a lot of the Book Loft in Columbus — it's a maze of rooms dedicated to books. There are so many used and second hand books to look through while you wind through what seems like endless rooms.
Belmont Army (Various locations)
Overall a cool vibe with cool products. Their prices are reasonable for vintage items!
AllSaints Spitalfields (700 North Michigan Avenue)
Even if you don't buy anything here (I never have), go just to see it. AllSaints is hands down one of the coolest retail environments I have ever been in. You'll especially love this spot if you are into sewing or industrial machinery and decor.
Reckless Records (Various locations)
If you like to dig for records, Reckless has a huge variety and knowledgable staff.
Randolph Street Market (West loop)
This flea market happens at the end of each month and is huge. It includes lots of vendors, both vintage and DIY, and you can get lost for hours.
The Vintage Bazaar (Location varies)
Another vintage showcase that'll suck you in and make you want to empty your wallet. Keep an eye out for their rotating schedule!
Lost Girls Vintage (Mobile Vintage shop)
Seriously, the entire Beehive Chicago space is amazing. Lost Girls Vintage always have pieces that I covet. They even have a great chevron Winnebago ("Winnie") that you'll find popping up around the city.
Museums & Touristy Fun
The Field Museum (1410 S Museum Campus Dr)
This is my favorite museum in Chicago. They have an outstanding permanent taxidermy exhibit, mummies, and of course Sue the T-Rex.
Museum of Science and Industry (1 57th St & Lakeshore)
I have great memories of MSI growing up. The traveling exhibits are engaging and fun. My favorite part is the "old timey" town, where there is even an old cinema where they loop silent films!
Lincoln Park Zoo (2200 North Cannon Dr)
For being a free zoo, LP is really rather nice. it's right in the city and if you stand at the bridge just south of the petting zoo, you'll see an amazing view of the city. I recommend the cat house, naturally.
Shedd Aquarium (1200 South Lakeshore Dr)
The Shedd is a bit pricey (and even on "free" days, you still have to pay to see the sharks and dolphins and what have you), but it really is a large space with a lot of intriguing exhibits and animals. The shark tank is eerily large and the reef section is colorful and fun.
Museum of Surgical Science (1524 North Lake Shore)
I stumbled upon this by accident while biking around one day. I went in on a free day and observed some skulls and skeletons and art regarding the human body. It's a fascinating museum in a fascinating old building.
Millennium Park (201 East Randolph)
This is a go-to. Everyone loves Millennium Park and Cloud Gate (more commonly known as "The Bean"). They have changing sculpture exhibits and the sometimes-forgotten Crown Fountain that's great for beating the summer heat.
The Skyline from Adler Planetarium (1300 S Lake Shore)
At night, make a point to go out on the peninsula and see the skyline in all of its glory. The photo at the top of this post was taken on a very cold January night in 2010 out on that spot!
Sears Tower Skydeck (233 South Wacker Dr)
Remember that scene in Ferris Bueller's Day Off where they're all leaning their faces against the glass and looking down on The Windy City? Well, Sears Tower (it will never be Willis Tower to me) can save the Windex, because in 2009 they opened the Skydeck. These glass boxes protrude from the side of the 103th floor, giving you a look straight down at the streets below. It's an unreal experience.
The Art Institute of Chicago (111 South Michigan)
Monet, Saurat, Picasso, Hopper, Grant, O'Keefe and more. Don't miss the Native American art and the new(ish) Modern Wing.
North Avenue and Montrose Beaches
These are my two favorite Chicago beaches. North out of convenience, and Montrose because of the atmosphere. Bring a towel and some snacks!
Magnificent Mile Shopping (Michigan Avenue)
Everyone has to experience this at least once. Michigan Avenue has some very interesting stores, albiet out of my price range, but it's certainly fun to look around. Surprisingly, the Forever 21 on Michigan Avenue is probably one of the better XXIs I've ever been in (as far as cleanliness, customer service, and organization). Pigs can fly, right?
Chicago Architectural Tours (Chicago River)
I have yet to do this but everyone raves about the Chicago boat tours. I have had many friends do this and they all say it's wonderful. Chicago has some pretty killer buildings, so why not take advantage of the river to learn about them?
Events & Parties
Movies in the Park (Various locations)
One of my favorite summer activities. No matter what neighborhood you're in, there's going to be a movie playing nearby somewhere.
Windy City Soul Club (1035 North Western Ave)
This happens once a month at The Empty Bottle in Ukrainian Village. I look forward to it every month and always have a blast.
Renegade Craft Fair (Varies)
Renegade is typically a good time. I hight recommend the summer event, because the winter one is just too crowded.
Chicago Summer Street Festivals (Everywhere)
Summer in this city is truly amazing and there's always something happening. Check out this list of what's going on where and get your butt outside!
The Cubs at Wrigley Field (1060 West Addison)
Get all American'ed up and enjoy some baseball! The stadium is super old and has the craziest vintage scoreboard ever. They offer veggie burgers and have tasty pretzels that any baseball fan has come to love. Opt to get your soft serve ice cream in a plastic Cubbies hat!
The Ferris Bueller Tour
While not an official "tour", check out the website and plan your route. Ferris Bueller's downtown scenes were all filmed in one day. Think about it!
Turtle Racing at Big Joe's (1818 West Foster)
This is just one of those weird things you need to see at least once.
Second City Comedy Club (1616 North Wells St)
Some of comedies greatest legends got their start here – John Candy, Tina Fey, Chris Farley, and more. Check out their shows and relax. Laughter is the best medicine.
Transportation
CTA (Everywhere)
The publics trains and busses in this city are an excellent way to get around the city. I recommend getting a day pass (1- 5- 7- or 30- day increments) so that you can ride unlimited!
Bikes (everywhere)
Chicago is very bike friendly and you'll notice bike lanes on almost all of the major streets. Stay safe and use lights at night. There is even a bike share service called DIVVY. Tip: it's illegal to ride on the sidewalk. Don't be that jerk!
Lyft (almost everywhere)
Better, cheaper, and more socially-responsible ride sharing than Uber.
Santullos has the best pizza in the city, in my opinion
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