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!
Food
Cemitas Puebla (west of Humbolt Park — 3619 West North Ave)
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. The spot was recently remodeled, but I'm so glad they opted to leave up the amazing wall of vintage photos. This is a don't miss. I'm serious.
The Chicago Diner (3411 North Halsted)
Vegans rejoice and get yourself a dairy-free milkshake. Thank me later.
Antique Taco (Wicker Park — 1360 North Milwaukee)
While their vegetarian menu is sparse (I do however love the Corn off the Cobb Salad!), it's worth it for the horchata milkshake. Can you tell that I have a thing for Mexican food...?
MELT Sandwich Shoppe (Bucktown —1840 North Damen Ave)
Reminiscent of the Cleveland version of the grilled cheese restaurant by the same name. I love that the dining space is laid out cafeteria-style. Plus the one wall is a chalkboard, so feel free to doodle your heart out. I discovered this place via Groupon and honestly... cheese. There are two vegetarian items on the menu and you can always get the others meat-free!
Gino's East (Various locations)
The tourist in me loves the location downtown near Michigan Avenue. The employees are always really friendly and their veggie pizza has asparagus on it! I'm not a huge fan of Chicago-style pizza, but this one is one of the better spots in my opinion.
Pequod's Pizza (Various locations)
Another good pizza spot. While I'm not a huge fan of their Lincoln Park space (it's odd and doesn't have a lot of character) the pie makes up for it. I promise. Note: there's a bad painting of Gandalf in the men's restroom.
The Boiler Room (2210 North California Avenue)
Okay, so this is a bar, too, but I really love it as a restaurant. They have a patio out back, Jameson-infused soft serve ice cream, and a special called the PBJ. What's a PBJ, you ask? Pizza, beer, and a shot of Jameson (yes, they love their Irish Whiskey). Their pies are flat and crispy (yum!), the space is really intriguing, and they have mirrored screens behind the bar that loop movies and skate videos. Keep in mind that it's cash only — but there's a trick to it. If you opt to get cash out at the ATM in the back of the bar, show your ATM receipt to the bartender and get a free shot of Jameson. Can't beat that, right?
Dos Amigos (2320 North Milwaukee)
It's almost laughable how much my friends and I go here. The burritos are cheap, delicious, and HUGE. They have late hours on the weekends to satisfy your late-night guacamole cravings.
Heavenly Gelato & Ice Cream Cafe (2662 North Sawyer)
Even though they have a sign outside that's reminiscent of those awful scrolling belt buckles from the early 2000s, I recommend checking this spot out. They even have some vegan flavors!
Kuma's Corner (2900 West Belmont)
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.
The Wormhole (1462 North Milwaukee)
This spot is easily my favorite coffee shop. There's a DeLorean and it's decorated with movie memorabilia from my childhood. The staff is über-babely and they have tasty drinks and treats. Not into coffee? Try the Rocket Sauce!
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!
Bars
The Owl (2521 North Milwaukee)
This neighborhood bar used to be a Mexican dance club (or so I hear). When the new owners took over, the only thing they decided to keep was the waterfall. Yep, a waterfall. And it's behind the bar. This spot gets packed on the weekends and is super chill during the week.
Bonny's 4AM (2417 North Milwaukee)
This 4am bar is probably one of my most frequented. It's not for everyone — in fact, it's where my friends and I like to go to "get weird." On weekends they have a couple of DJs and it becomes a crowded dance party. During the week it's rather empty. The bartenders are beyond awesome, but keep in mind that it's cash only. Bonus: they have a photobooth.
Danny's (1951 West Dickens)
They host The Smiths night. That's all you need to know.
Club Foot (1824 West Augusta)
One of my friends dragged me here for the first time a few years ago and I ended up being really into it. First of all, the name is brilliant, and if you have any ounce of nostalgia in you, you'll be oogling at the walls lined with vintage toys and oddities.
Three Aces (1321 West Taylor)
Gedi recently introduced me to this place and it has a nice vibe. 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.
Longman & Eagle (2657 North Kedzie)
A whiskey bar with some of the best branding I've seen in a while. Count me in!
The Rocking Horse (2535 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.
Shopping
Rudy's Roundup (1410 North Milwaukee)
Rudy's has been one of my favorite stops for years! They boast themselves as a "modern general store" but they are much more than that. They have tons of great gift items, knick knacks, and even some clothing. Give yourself enough time to discover everything!
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!
Urban Outfitters Surplus (2352 North Clark)
Urban's only "outlet" in the company is right in Lincoln Park. If you haven't been here yet, you're missing out big time. A majority of the store is under $20 and you can find designer duds for ultra-cheap. And the staff is mighty fine lookin' if I do say so myself.
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)
Music, music, music. I could get lost in here forever.
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!
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 always a good time! I love checking out prints by local (and not local) artists. Easily, my favorite part is the jewelry!
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. Tip: it's illegal to ride on the sidewalk. Don't be that jerk!
Uber (everywhere)
This smart-phone based cab service is incredible. I've only recently been using them, but you can request a cab or fancy black car to pick you up at your desired location. If you've ever tried calling for a cab on the phone in Chicago, you know that it's pointless. Uber actually tells you how long (and shows you on GPS) until your cab arrives. Plus the tip is included in the fair and it takes it straight from the account that you have linked to your profile. Killer!
