Chicago, Illinois
When I left Chicago, I drew a city guide for the rest of the gals on my dorm floor of all my favourite places. I wish I’d copied it or taken a picture so I could include it here. However, I’ll offer you the next best thing: my recollected favourite places in the city, written down in digital form so you can access it on your adventures.
Chicago is hands-down one of my favourite cities in the entire world (and I’ve traveled quite a bit). She’s honest and beautiful and anyone can belong and I love that. I found some of the best parts of myself by exploring neighborhoods, observing strangers on the train, trying new fashion by way of the thrift stores, and shooting shows in her iconic venues. I hope you find inspiration in this city and find beautiful parts of yourself, too.
walkability & transit
Chicago is super walkable. If you’re visiting, I would definitely recommend avoiding bringing a car because finding parking and paying for parking are more of a hassle than it’s worth.
One of the things I love the most about Chicago is that you don’t need a car. You’ve got your legs and the train and a bus and that’s all you need. You get there when you get there. And there’s so much inspiration to be found in the crowded hubub of the train and the bus. You overhear stories and find fashion inspiration and are a character in other people’s lives and I love that.
My recommendation would be to get an unlimited public transit pass. They have 1, 3, 7, and 30 day options and you can use them for the train (the L, not the Amtrak) and the bus. Then you don’t have to worry about finding a station to reload your card or having cash for the bus and if you take the wrong train—no big deal! You can hop off at the next station and switch directions at no extra cost. It’s definitely going to save you money and hassle in the long run to get one of these for your adventure. Between walking and public transit, you’ll be set.
I’d recommend Google Maps for transit and walking directions—just be sure to put it on silent or use headphones, so everyone else doesn’t hear that you don’t know where you’re going! It’s okay to ask for help if you get lost, but it’s also safest not to announce via a loud app that you have no idea where you’re at—you know?
neighbor
hoods
The way this guide is split up is by category. However, if you’re looking to just post up and explore a neighborhood yourself, I wanted to also give you a few starting points!
I lived in the Near North neighborhood, but it’s not a super exciting area to wander around, so we aren’t including that. I’ll include the name of the area, but also the train stop or bus line and stop I’d get off on in order to explore.
If you want to get more of a taste of the creative community in Chicago, I’d recommend starting somewhere like Logan Square. It’s less commercialized than Wicker Park, but still super fun and creative. If you’re looking for a downtown experience, Michigan Avenue or State Street will give you that. If you want a best-tacos-best-thrifting spot: Roscoe Village all the wall (more on that later).
If you want to explore downtown near Michigan Avenue:
Red Line: Chicago stop
66 bus: Chicago & Michigan
If you want to explore downtown near State Street:
Red Line: Lake Stop
Blue Line: Washington stop
If you want to explore Wicker Park:
Blue Line: Damen or Division stops
If you want to explore Logan Square:
Blue Line: Logan Square stop (self-explanatory)
If you want to explore Northalsted:
Red or Brown Lines: Belmont stop
If you want to explore Roscoe Village:
Brown Line: Paulina stop (and about a 10-minute walk)
If you want to explore Lincoln Park:
Brown Line: Armitage stop (there are other stops for Lincoln Park, too—this spot is my favourite though)
If you want to explore Wrigleyville:
Red Line: Addison stop
coffee & tea
So I went to college in Chicago, which meant I had almost no money and almost every meal was on campus. It also meant that I mostly explored by going to coffee shops, thrift stores, and music venues, so you’ll find this guide to strongly favor those sorts of places. Now first off: coffee. This is first because no matter what time I arrive somewhere, I will definitely need some type of caffeine.
Plus, if you find a good coffee shop, it usually puts in you a cool neighborhood, which is a fun launching place to explore.
Some of these spots are more down-to-earth and some are a little more pretentious, but don’t let that stop you from asking your barista for coffee recommendations or for just cool spots around the neighborhood. People are people and most people are pretty awesome.
Big Shoulders Coffee
Neighborhood: West Town (they have a couple locations, but this one is my favourite)
Address: 1105 W. Chicago Avenue, Chicago, IL 60642
Transit access:
66 bus, Chicago & Milwaukee stop
Blue Line, Chicago stop
Food: breakfast food and pastries
Vegetarian/vegan options: veggie burrito, almond milk, oat milk
This has become one of my favourite spots. It’s just slightly off the beaten path and the baristas are the kindest I’ve met in the city. Try their marshmallow latte—I promise you won’t regret it.
Bourgeois Pig Cafe
Neighborhood: Lincoln Park
Address: 738 W Fullerton Ave, Chicago, IL 60614
Transit access:
Red Line, Fullerton stop
Brown Line, Fullerton stop
Food: breakfast food and sandwiches
Vegetarian/vegan options: veggie panini, salads, fruit bowl, toast
One of my favourite bands posted that they loved this coffee shop, so clearly I had to go there. I spent many mornings and afternoons editing in this cozy spot. My go-to drink at the time was a mocha bianca, which I think is basically a white chocolate mocha. It’s sweet, but if you’re into that, it’s worth a try!
Sawada Coffee
Neighborhood: West Loop
Address: 112 N Green Street, Chicago, IL 60607
Transit access:
Blue Line, Grand stop
Green Line, Morgan stop
Pink Line, Morgan stop
20 Bus, Madison stop
Food: pastries
Vegetarian/vegan options: most of the food is bread-adjacent—not sure if it has milk in it, so possibly
This spot is close to Soho House, so you can explore both in one trip!
Heritage Bikes and Coffee
Neighborhood: Lakeview (they have a couple locations, but this one is my favourite)
Address: 2959 N Lincoln Avenue, Chicago, IL 60657
Transit access:
Brown Line, Diversey stop
Red Line, Belmont stop
9 bus, Ashland and Wellington stop
77 bus, Belmont and Southport stop
9 bus, Diversey and Lakewood stop
Blue Line, Chicago stop
Food: salads, wraps, burritos, pastries
Vegetarian/vegan options: vegan crunch wrap, pastries
This combination bike shop / coffee shop is a fun stop in the Lakeview neighborhood!
donuts
When I lived in Chicago and the few years immediately after, I was very into donuts. Like I photographed for a donut shop and tried donuts in every city I visited and bought a ticket to a donut festival. I was not playing games.
But on the flip side, what I love about donuts and donut culture is the levity. You can’t be too serious while eating a donut and the environment is open and accessible, both in the lack of status and the lower price point than a lot of treats.
Doughnut Vault
Neighborhood: River North
Address: 401 N Franklin Street, Chicago, IL 60654
Transit access:
Brown Line, Merchandise Mart stop
Coffee: yes; hot coffee and cold brew
Gluten-free or vegan options: I could not find any on their menu
This spot is a hidden gem. They always sell out and they often have lines, but if you get there early enough, you’re in for a treat! Keep in mind that the space is super small—they’re not joking when they say “vault”—and there is very little seating (possibly no seating with Covid).
Stans Donuts
Neighborhood: Wicker Park (they have a gazillion locations, but this is the one I’ve been to)
Address: 1560 N. Damen Avenue, Chicago IL 60622
Transit access:
Blue Line, Damen stop
Coffee: yes; hot coffee, cold brew, nitro cold brew, lattes
Gluten-free or vegan options: yes to both! Check out their menu here.
Stans also has tea, smoothies, and sandwiches, though I haven’t tried anything but the donuts and coffee (this surprises no one). The vibe of the shop is cute, too, and a great spot if you’re looking for a little treat.
thrifting
I wasn’t lying when I said I basically just drank coffee and thrifted. Also, I am sure Chicago has amazing vintage stores, but I was basically broke, so I explored deep into the thrift stores, the ones with cheap prices and rows and rows of buried treasures. Two of my all-time best thrift finds—my No Doubt tee and my Bryan Adams long-sleeve—were both found in these store.
I’ll swear by Chicago having the best thrift stores… but I’m open to being proved wrong. Send me your favourite spots!
I would skip the Goodwills in Chicago; I’ve never found anything good. The Salvation Army closest to downtown is super hit-or-miss, so again: probably not worth your time. However, if you have time and you want an adventure, I have nothing but good things to say about the Village Discount Outlets.
Pro tip: they often don’t allow backpacks, even the purse or camera bag kind (and I don’t love checking wallets or cameras at the register), so I’d recommend leaving a larger back in your trunk or at your hotel.
They also don’t often have fitting rooms, so I’d recommend wearing leggings or yoga pants/shorts and a top that you can try clothes on over (there’s usually a mirror for this purpose).
Village Discount Outlet
Neighborhood: Roscoe Village (this is my favourite one)
Address: 2043 W Roscoe St, Chicago, IL 60618
Transit access:
Brown Line, Paulina stop
This is my favourite thrift store in all of Chicago. They have tons of stuff, but you’ve got to hunt for it. If that’s your jam, this is your place. It’s also only a short walk away from my favourite taco place, Tony’s Burrito Mex.
Village Discount Outlet
Neighborhood: Logan Square (yes, it’s the same chain—different location)
Address: 2032 N Milwaukee Avenue, Chicago, IL 60647
Transit access:
Blue Line, Western stop
This is my second favourite thrift store, or at least it’s tied for second with the Family Thrift down the street. The best part of these two shops is you can hit them both up on the same adventure.
Family Thrift
Neighborhood: Logan Square (just a few blocks from Village Discount, so you can make a thrifting day out of if if you’d like!)
Address: 2160 N Milwaukee Avenue, Chicago, IL 60647
Transit access:
Blue Line, Western stop
This is where I found my vintage Bryan Adams longsleeve tour tee. It’s a gem of a thrift store and worth the treasure hunting.
music venues
Chicago is where I began shooting shows, so the venues in this city hold a fond place in my story. If you’re planning a trip to the city, check out their upcoming events pages to see if you can catch a cool gig while you’re in town!
These are listed in no particular order other than by my recollection.
House of Blues
Neighborhood: River North
Address: 329 N Dearborn Street, Chicago, IL 60654
Transit access:
Blue Line, Clark and Lake stop
Brown Line, Merchandise Mart stop
Red Line, Grand stop
Capacity: 1,800
This venue is where I shot my first show, so it holds a place of fondness in my recollection.
Beat Kitchen
Neighborhood: Roscoe Village
Address: 329 N Dearborn Street, Chicago, IL 60654
Transit access:
50 bus, Damen and Belmont stop
77 bus, Belmont and Hoyne stop
Brown Line, Paulina stop
Capacity: 275
Metro
Neighborhood: Wrigleyville
Address: 3730 N Clark Street, Chicago, IL 60613
Transit access:
22 bus, Clark and Waveland stop
Red Line, Addison stop
Brown Line, Southport stop
Capacity: 1,100
Lincoln Hall
Neighborhood: Lincoln Park
Address: 2424 N Lincoln Avenue, Chicago, IL 60614
Transit access:
Brown Line, Fullerton stop
Red Line, Fullerton stop
Capacity: 507
Schuba’s Tavern
Neighborhood: Lakeview
Address: 3159 N Southport Avenue, Chicago, IL 60657
Transit access:
Brown Line, Southport or Belmont stops
Red Line, Belmont stop
77 bus, Belmont and Southport stop
Capacity: 165
I photographed Billie Eilish for the first time here!
United Center
Neighborhood: River North
Address: 329 N Dearborn Street, Chicago, IL 60654
Transit access:
Blue Line, Clark and Lake stop
Brown Line, Merchandise Mart stop
Red Line, Grand stop
Capacity: 1,800
Cafe Mustache
Neighborhood: Logan Square
Address: 2313 N Milwaukee Avenue, Chicago, IL 60647
Transit access:
Blue Line, California stop
74 bus, Fullerton and California stop
Capacity: I didn’t find an exact number online, but it’s also a coffee shop, so it’s relatively small.
food
The main reason I’m sharing this section is to direct you to what is my favourite taco shop in the whole entire world. And it’s literally a short walk from my favourite thrift store (the Roscoe Village Village Discount Outlet) in the entire world, so now you get a snapshot of my ideal day.
Also, there’s not a category for “free stuff you can get while in Chicago” (and if I’m being honest, I don’t know with Covid if they’re still doing this), but traditionally if you visit the Ghirardelli store off of Michigan Avenue, a greeter will offer you a wrapped piece of chocolate when you walk in. Definitely worth a stop.
Tony’s Burrito Mex
Neighborhood: Roscoe Village
Address: 1957 W Belmont Avenue, Chicago, IL 60657
Transit access:
Brown Line, Paulina stop
77 bus, Belmont and Damon stop
Price: $2-10
Food: tacos, burritos
Vegetarian/vegan options: vegetarian taco and burrito
Protein Bar
Neighborhood: River North
Address: 352 N Clark Street, Chicago, IL 60654
Transit access:
Brown Line, Merchandise Mart stop
22 bus, LaSalle and Hubbard stop
Price: $7-15
Food: breakfast, bowls, wraps, burritos, smoothies, coffee
Vegetarian/vegan options: “Superfood Vegan” wrap, Beyond Meat parm, Beyond Meat spicy Korean bowl
This is a chain with several locations around the city. I listed the one I most often frequented, but they’re all basically the same.
Chicago Diner
Neighborhood: Lakeview
Address: 3411 N Halsted Street, Chicago, IL 60657
Transit access:
Red Line, Belmont stop
Brown Line, Belmont stop
36 bus, Broadway and Roscoe stop
22 bus, Clark and Roscoe stop
Price: $10-20
Food: vegetarian Americana
Vegetarian/vegan options: all the things!
If we’re being honest, I think I found this place because I heard that Hayley Williams liked it. It’s one of the OG vegetarian spots in Chicago—and it has milkshakes! There’s also a location in Logan Square.
Native Foods
Neighborhood: Wicker Park
Address: 1484 N. Milwaukee Avenue, Chicago, IL 6-622
Transit access:
Blue Line, Damen stop
Price: $7-20
Food: burgers, bowls, dessert
Vegetarian/vegan options: all the things!
Yes, Native Foods is a chain, but it’s also fond to me because it was the first time I remember eating plant-based food and thinking, “wow, this is really good!” Maybe that had more to do with my college “vegetarian” options being essentially iceberg lettuce and fries and less to do with vegetarian food itself. That’s a long story to say: this place is great.
Pizza
Okay, so instead of recommending one place, I’m going to give you your options. Pizza is a very controversial topic in Chicago and everyone has their favourite. My go-to is usually Lou Malnati’s, but I’m honestly not too picky about it. I’ll eat deep dish pretty much anywhere (I know, that probably doesn’t make me a true Chicagoan). There are a lot of locations for each place, so I’m not listing the addresses this time. Also keep in mind that deep dish normally takes a long time to cook, so plan an hour or two for your meal!
Gino’s East (but everyone just calls it Gino’s)
Portillo’s
Neighborhood: River North
Address: 100 W Ontario Street, Chicago, IL 60654
Transit access:
Blue Line, Clark/Lake stop
Red Line, Grand stop
66 bus, Chicago and Clark stop
156 bus, LaSalle and Ontario stop
Price: $5-15
Food: hot dogs, beef sandwiches, burgers, pasta
Vegetarian/vegan options: basically salads and fries
Listen, Linda. Yes, it’s touristy, but this is the place for a hot dog in Chicago. And it was my go-to spot to grab a bite after shooting a show, since it was on my walk back from House of Blues. If I was super hungry, I could grab a hot dog, but I’d usually just get a cake shake, which is exactly what it sounds: a giant piece of chocolate cake blended into a shake. I do not recommend this if you’re lactose intolerant as it will probably break you, but if you eat dairy: this will change your life. It’s one of my favourite treats of all time.
Soho House / The Allis
Neighborhood: West Loop
Address: 113-125 North Green Street, Chicago, IL 60607
Transit access:
Pink Line, Morgan stop
Green Line, Morgan stop
Blue Line, Grand stop
Price: $7-30
Food: breakfast, salad, pizza, tea, cocktails, wine
Vegetarian/vegan options: yes, some soup, salad, and entree options
I had the very first avocado toast of my relatively young life (at the time) at Soho House, so you could say that this place was quite monumental for me. Basically, it’s the entire reason I don’t own a house right now (if you don’t get the joke, google millennials and avocado toast). In sincerity, the place is beautiful and a great place to enjoy a meal.
The Atwood
Neighborhood: The Loop
Address: 1 W Washington St, Chicago, IL 60602
Transit access:
Red Line, Lake stop
Blue Line, Washington stop
36 bus, State & Washington stop
22 bus, Clark & Randolph stop
Price: $10-30
Food: breakfast, lunch, coffee, wine, cocktails
Vegetarian/vegan options: salad, waffles, oatmeal, avocado toast (some of these do have some dairy)
Was this the best meal of my life? No. But is this restaurant designed by the same architect who was in charge of the 1893 Chicago World’s Fair? Yes. And did I devour The Devil in the White City and absolutely have to go see this spot? Heck yes. So if you loved that book like I did, it’s worth treating yourself and checking out a bit of Chicago’s history.
shopping
I didn’t shop a lot (outside of thrifting), but when I did, these were a few spots I enjoyed.
Art Effects
Neighborhood:
Address:
Transit access:
Reckless Records
Neighborhood:
Address:
Transit access:
touristy stuff
I was one of those annoying college kids who thought: “i WoN’t ViSiT tHe MuSeUmS. i LiVe HeRe. ThAt’S tOo ToUrIsTy AnD i’M nOt A tOuRiSt.”
And now I am a full-grown adult person who no longer has a student discount and wants to go to the museums and regrets her adolescent pretension.
Don’t make my mistake. Like what you like. Enjoy what you enjoy. If it’s peripheral stuff, awesome. But if you genuinely want to enjoy the tourist attractions the city has to offer: do it! I’ll point you in the direction of some of my favourites and what I think are worth the money.
The Bean
Neighborhood:
Address:
Transit access:
Cost: free!
It’s fun, it’s cheerful, it’s free, and it has a great view of the city when you look back. In my opinion, this is one of those touristy things that’s worth doing at least one.
the end
It’s not really the end though. Because I’m always learning. There’s always old places closing and new places opening and places that have always been there that I just haven’t seen yet.
If you have recommendations of other places in Chicago or other cities to check out, email me! I don’t have an email address for this site yet, but I’ll link the contact page of my personal site here.
