Green City Guide: Chicago
In the 1830s, even before it officially incorporated as a city, Chicago claimed the motto “Urbs in Horto” meaning City in a Garden. Green space has always been a central concern, and even as industry continues to grow, and technology continues to develop, natural areas keep getting set aside and new parks keep opening.
Chicago is a giant city and it’s impossible to see and do it all. After more than a dozen years of living here, I know it well, but there are still so many neighborhoods I haven’t even set foot in. Below you’ll find a guide to some of my favorite places here: public parks, shops, vegetarian-friendly restaurants, bars, cafes, museums, and music venues.
I’ve organized this guide by type of attraction, but included each place’s neighborhood in the headline. My recommendation would be to zero in on a couple of neighborhoods you’d like to explore and plan from there. And if you’re not able to see/eat everything you wanted to, just start planning your return trip. If you have specific questions, feel free to get in touch!
Public Green Spaces
Downtown
Millennium Park is Chicago’s green crown jewel. I moved to the city back in 2003, just before the park was being finished and from the get-go, it was a stunner. Wander in from any entrance, watch the city lights flicker in the reflection of The Bean, breathe deep the scent of Russian Sage in Piet Oudolf’s Lurie Garden. The newly opened Maggie Daley Park is the most impressive playground I’ve ever seen and a fantastic place for families to wander over to. To get to the gorgeous lakefront, a chain of cityfront beaches and biking/running paths, either walk the length of Michigan Avenue all the way past Oak Street, or hop on a Northbound bus.
Vietnam Veterans Memorial / Chicago Riverwalk
Downtown
This is a bit of a hidden spot, right in the middle of downtown Chicago. Giant steps lead you down to a grassy space dotted with trees (and in the spring, crawling with tiny, fuzzy caterpillars). This is a great place to bring your lunch for a picnic, or just sit for a while to escape the crowds on Michigan Avenue. For many years, the Vietnam Memorial was one of the few accessible areas right along the Chicago River. Now, most of the Riverwalk is continuous and connects multiple places to stop and watch the water taxis go by.
Downtown
This lush little park is directly in front of the Newberry Library and filled to the brim with luscious plants and blooms. A classically designed garden, all paths lead to the central fountain. Grab a bench if you can, there’s lot of people watching to be done as the park is nestled in the very fancy Gold Coast neighborhood.
Garfield Park
A must-visit if you happen to be traveling to Chicago in the winter (in which case, my condolences). The Garfield Park Conservatory is not the easiest conservatory to get to (that would be the Lincoln Park Conservatory), but it is certainly the most impressive. Wander through the huge collection of tropical plants, ferns, orchids, cacti, aroids, and more. There are eight huge greenhouses and many more acres of outdoor gardens to explore. Bring a lunch and a book. Once you’re there, you won’t want to leave.
Lincoln Square
If you find yourself on the north side of the city, a trip to Winnemac Park would be a well-planned detour. There are over 40 acres of park to relax in, landscaped with huge oaks and weeping willows, as well as a large prairie, filled with plants native to the Midwest. The folks that live in this area take Fourth of July very seriously, so either come prepared (with tons of fireworks bought in Indiana) or seek shelter.
Logan Boulevard / Palmer Square Park
Logan Square
The stretch of Logan Boulevard between Western Ave and Kedzie comes alive in the summer. Locals bring out the picnic blankets and the grills and take over. Some years, you’ll find a large scale impromptu flea market run and organized completely by local residents. If lounging or browsing isn’t your thing, every Sunday the Logan Square Farmers Market opens up and offers up some of the region’s best produce, breads, cheese, pantry goods, and snacks. Want more? Logan Boulevard and Palmer Street are both lined with some of the city’s most beautiful greystones and turn of the century mansions. And after walking around Palmer Square Park, reward yourself with a stop at Miko’s Italian Ice.
Hyde Park
The site of the 1893 World’s Columbian Exposition, Jackson Park is over 500 glorious acres of public green space on the city’s south side. The beloved Museum of Science and Industry is nearby, and is housed in the only building from the Exposition that survived. Wander through the park’s grasslands and over the bridge onto Wooded Island where the Osaka Garden was planted centuries ago for the Fair. A good bit of Jackson Park is currently under construction, but if you’re in the Hyde Park or Woodlawn area, it’s still a destination worth mentioning.
Glencoe IL
Getting here requires a bit of a hike, but you’ll be rewarded well for your adventurous spirit. There are dozens of gardens and greenhouses to explore, all themed, beautifully planted, and extremely inspiring. The Japanese Garden, Fruit & Vegetable Garden, and Evening Island are some of my favorites. You can take the Metra train up to Glencoe, or if you’re feeling particularly intrepid, there’s a bike path that leads all the way there from the city. Entrance to the Garden by bike or on foot is free 365 days a year.
Where to Shop
West Town
I realize not everyone traveling to Chicago will have the luggage capacity to purchase houseplants, but I can’t help but include some beloved plant stores on this list. Sprout is impressive because of both their quality and quantity. They always have interesting and unique species, and tons of em. I find myself going through this store at least three times: first just to browse, then again to pick up all the plants I want to buy, then a third time to put back most of my choices because I remember that I am a plant hoarder.
Old Town
You will want to live in this store. Exposed brick walls, sky high ceilings, and rough and reclaimed accessories nestled between a beautifully curated selection of plants and cut flowers. The store doubles as an event space, including the back patio which has a great variety of terra cotta pots. Check out the basement for imported tchotchkes, vintage tiles, every color of ribbon, and perfect, simple, white candles in all shapes and sizes.
Logan Square
This is where I bought my prized euphorbia trigona which started out about a foot tall, and now is about as tall as I am. Their plants are beautiful and well taken care of, but their flower selection is really where this place shines. They carry every shape, color, and texture you could want, and the staff is kind and very patient. Check out their selection of gifts and candles too — they carry some of my favorites from Tatine and P.F. Candle Co.
Wicker Park
Get lost in three levels of used and vintage books, one of the largest and most diverse inventories in the city. Myopic has been around for as long as I’ve lived here, and definitely long before that. It’s a cornerstone of any north side book lover’s life. Once you’ve eaten your fill of donuts from Stan’s, spend the afternoon catching up on some reading while you digest.
Humboldt Park
I dare you to walk in this store and not be equally inspired and intimidated by Claire, the owner’s, perfect taste. She has an uncanny talent for seamlessly blending clean, elegant, midcentury style with the unapologetically handmade, the warped and woven, the warm and muddy and the glittering gold. Buy all the furniture, vintage kilim rugs, and contemporary housewares and jewelry and just ship it back to your house. The stunning houseplants (Oh, the plants!) are not for sale, but if you’re still jonesing, you can stock up at the universally loved Adams & Son right down the street.
Lincoln Square
One more plant store! The one specializes in terrariums as well as local and handmade goods. This spot is all about the details. The particular feel of a rippled, ceramic vessel in your hand. The way a succulent’s flower reaches toward the filtered light from the window. The look of all these colors and textures playing off one another. Bonus points to Marco, the owner, for being the nicest and most helpful guy in the world. His store is also the reason why my apartment constantly smells of the piñon incense from Juniper Ridge.
Wicker Park/Ukrainian Village
Browsing for vinyl has never been a more pleasant experience than it is here. They have an incredibly wide range of genres though their jazz, soul, and world section are of special note. Everything is extremely well organized and in really great condition. If you’re brave and have a lot of time on your hands, head downstairs to the bargain basement where thousands of gems (and invariably some stinkers) are waiting to be discovered.
Ukrainian Village
I don’t find myself often pining for clothes (I’d usually rather spend the money on food or plants), but Penelope’s always makes me rethink my entire wardrobe. Classic silhouettes, simple, quality construction, neutral colors, and fun prints. I always find myself coming back to their outstanding assortment of round sunglasses. A great store to stop in while wandering down Division Street.
Where to Eat
Wicker Park/Ukrainian Village
Now we’re getting to the really good stuff! This is my favorite vegetarian restaurant in the city. Small plates, sake cocktails, super cozy atmosphere, and wonderful, warm staff. Everything they serve here is delicious and incredibly flavorful, but the Mana Sliders are a classic. During the summer, seating just about doubles in their outdoor tent.
Ukrainian Village
A dear neighborhood favorite when I still lived in Ukrainian Village, the kitchen at Bite Cafe does it right. Stop by before a show at the Empty Bottle next door. Extremely tasty and vegetarian friendly for brunch or dinner (these are the only two meals in Chicago).
Ukrainian Village
Walking into this bright, beautiful restaurant makes me think I’m suddenly in Los Angeles or Seattle. Scrumptious brunch, avocado toast, grain salads, strong cocktails.
West Loop
In 2016, Chicago witnessed a wave of new restaurants opening that all called themselves “vegetable-focused.” Do not be fooled by the imitators. Bad Hunter is the best. Ample vegetarian options, a separate vegan menu, a fantastic beverage list with natural and orange wines (if you’re into that sort of thing, and I am), plus a staff that is deeply kind, funny, and considerate. I love this place.
Wicker Park
Actually, you don’t have to pick sides. No matter which one you choose, the prize is amazing tacos, so either way you win. Big Star’s giant outdoor patio is Wicker Park people-watching at its finest. Antique Taco has daily agua frescas and Bang Bang key lime pie on the menu (see below). You can’t lose.
Logan Square
I’ve never had better pie or customer service. The Pie Garden is where dreams (of pie and biscuits) come true. Literally every single one of their pies is the best pie that I’ve ever had. Can I say more wonderful things about this place?
Logan Square
I am in love with this restaurant. Everything on the menu is delicious and perfect. There are fantastic options for vegans, vegetarians, and omnivores. The atmosphere is so cool, and the food is made with so much care and attention to detail. So many of my fondest memories of times spent with the people I love happened in this spot.
Logan Square
I have a separate pizza stomach and it is bottomless, especially where Boiler Room is concerned. They’ve got giant, fantastic vegetarian pies on the menu, but their hummus plate is a secret stunner. Really, everything here is so, so good. End your meal with their boozy Jameson soft serve!
Logan Square
Another excellent pizza option in Logan Square, for when you’re hankering for more of a Neapolitan-style pie topped with tangy marinara and creamy burrata chunks. You will keep eating even after you think you’re full. See above statement about pizza stomachs.
Logan Square
Their menu may not seem like the most vegetarian-friendly. You may look at your veg options and think there aren’t enough dishes. But then you’ll order them all, wolf them all down, and even consider ordering a second round before you realize you’re comfortably full and incredibly satisfied. Parachute has thought it all through. Everything on their menu is well-considered and amazing. Not surprising as they were named one of Bon Appetit’s top 10 new restaurants in 2015.
Lincoln Park
If you came to Chicago and refuse to leave without trying deep dish pizza, make sure it’s worth your while. Pequod’s is the one that even Chicagoans keep coming back to. The crispy, burnt, cheesy crust edges are, simply put, heaven. Just make sure you call ahead because the wait can be brutal (especially when all you can think about is pizza).
Lincoln Square
The best burrito in Chicago. Seriously. It transports me back to my Los Angeles youth, where I was raised on refried beans and bouquets of cilantro. Also, the staff is the absolute best. If you’re so inclined, get the vegetarian burrito + cheese + avocado and a side of limes.
Downtown
I know what traveling can be like. Sometimes you just don’t leave downtown. I get it. So when you’re here and downtown and desperate for a quality meal that’s not too touristy and won’t break the bank, go to Quartino. This place is huge and definitely gets crowded on weekend evenings, but it’s delicious and great for large groups. The carafes of wine and tasty pizzas keep me coming back (yep, pizza AGAIN).
Downtown
Another great choice if you’re downtown. Some of the best Cuban sandwiches and Cuban coffee in the city. I like to go to the one on Congress St and take my food out to Grant Park for some al fresco dining. Plus great views of Buckingham Fountain aren’t far off.
Hyde Park
Half Indian cuisine, half soul food. It’s inexplicable, but it’s the best. I practically lived at this shoebox of a restaurant back when I was going to school in Hyde Park. It’s truly amazing. And also one of the few places you can get straight passionfruit juice in the city of Chicago.
Hyde Park
Back in the day this storefront used to be called University Market and their claim to fame was their delicious deli sandwiches made with fresh ingredients on chewy, crusty baguette. Well, U-Market eventually closed and Z&H moved in. A few things changed, they installed some big, fancy new windows, but they kept the same sandwich menu! Change doesn’t always have to be bad.
Where to Drink
Logan Square
Phenomenal tiki bar in the heart of Logan Square. You’ll think you’re somewhere far, far away (read: warm). Try to stop yourself at two drinks. They are tasty, they go down quick, and they pack a punch.
Logan Square
A bit far west, but certainly worth the trip. They specialize in classic, well-made cocktails. Gorgeous black and white photography on the walls, vintage shuffleboard table on the side, old photo both in the back. What’s not to love?
West Town
Possibly the smallest bar in the city, but with some of the best cocktails. I still think this was the best mojito I’ve ever had. They expand their seating outside in the summer (crucial for this spot that I think only has room for like 5 bar stools).
Lincoln Square
Comfortable and contemporary ambiance, a giant, seasonally-inspired drink list, and the world’s most perfect bar snacks. If you’ve never tried fried cheese curds, get yourself to this bar asap.
Humboldt Park
Back when I lived a few blocks away, this was one of my favorite bars in the city. It was a giant, moodily lit vintage bar with leather booths and grape soda on tap. Since then, they’ve renovated a bit, upped the price of drinks, and done away with the grape soda, BUT the place is still a strong contender. The expanded stage means more live music, which is always a plus. And I highly recommend their amazing Hemingway Daiquiri.
Pilsen
Fantastic drinks, super savory food (order the vegetarian version of the fried green tomato BLT), and live music just about every night. If you like BBQ and/or copious vintage paintings of deserts and cowboys, you’ll like this place.
Game Room at Chicago Athletic Association
Downtown
As you might have guessed, this spot used to be a members-only club for rich and well-connected Midwestern men. After sitting empty for many years, it reopened in 2015 as a public hotel with five (five!) bars. The Game Room is my favorite, as it’s got giant, gothic fireplaces, deep leather chairs, free (free!) billiards, and reasonably priced drinks.
West Loop
One of the best cappuccinos I’ve ever had. This place is industrial and very cool. It’s a great place to sit and enjoy the parade of fancy people walking down the street outside. Most importantly: the coffee is absolutely incredible and they also sell perfectly soft and crunchy donuts in an array of tasty flavors.
West Town
The best local coffee roaster in town. Consistently amazing coffee, and even more consistently delightful customer service. This light, bright cafe is warm and welcoming, plus they also sell Lucila’s amazing alfajores (if you’d like something sweet to go with your espresso).
Lincoln Square
My second home. The place I go most often when I’m not at work or at my house. The staff is the warmest, funniest, most genuine group of people in the world. The bagels are wonderful and filling, the cappuccinos, perfect every single time. If you get there early enough, definitely get a chocolate donut (brought in fresh everyday from Bennison’s in Evanston).
Where to See a Show
Pritzker Pavilion / Millennium Park
Downtown
There’s nothing better than sitting out at the Pritzker Pavilion on a warm evening. The radiant Frank Gehry bandstand reflects all the lights and colors of the summer sunset and provides the perfect backdrop for an outdoor picnic. Bring a blanket, some snacks, and a bottle of wine. Check the Department of Cultural Affairs website for a full calendar of events, most of which are free!
Downtown
More excellent free events happen here, just across the street from Millennium Park. Excellently curated rotating exhibitions and live music in one of the city’s most beautiful examples of a Beaux-Arts style building. Check out the stained glass ceiling upstairs, it’s the largest Tiffany dome in the world.
Downtown
Some of the best contemporary art exhibits I’ve ever seen. Massive Change and Olafur Eliasson were of particular note. Check out anything curated by the brilliant Naomi Beckwith. They also hold some phenomenal live theater, artist talks, music workshops, and film screenings as part of their MCA Stage programming.
Intuit: The Center for Intuitive and Outsider Art
West Town
The only non-profit arts organization in the U.S. that just presents outsider art. Check out the Henry Darger room, an installation that recreates the artist’s living space with actual artifacts from his nearby apartment. The exhibitions are always changing, and entrance to the gallery is just a suggested $5 donation.
Lincoln Square
There’s no conflict of interest. Even if I didn’t work here, I would still recommend it because it’s a truly impressive place. The Old Town School has been around since 1957 and is the largest community arts organization in the country. Classes for adults and kids, music and dance workshops, open jams, an archival resource center, a fully stocked music store, and over 400 concerts a year in two halls. The weekly World Music Wednesday series is my favorite and is free with a suggested $10 donation.
Pilsen
Bigger name acts tour through this beautiful old theater that was resurrected and reopened in 2014. This is a great place to wrap up an afternoon or evening exploring Pilsen, a historically Mexican neighborhood on the near south side that is being rapidly developed. The folks booking this venue acknowledge and celebrate its unique location in the city, and put on acts that prove it. I’ve seen both Low and Meshell Ndegeocello here, to wildly diverse crowds that were both having the time of their lives.
Roscoe Village
I absolutely love this place. Their lineup is mostly jazz (all types of jazz, from the straight ahead all the way to the completely out there) with some miscellaneous contemporary thrown in. The music is excellent across the board, the room is small and intimate, and the vibe is extremely relaxed. There are cool jazzers wearing tiny glasses and all black, and there are completely approachable, regular folks. The bar is darkly lit and well stocked. Favorite shows I’ve seen there include Rodrigo Amarante, Melaku Belay Fendika, and Amy Schumer.
Uptown
Another excellent place to see exemplary jazz. Even if your trip to Chicago is short, a trip to the Green Mill is pretty essential. No-nonsense cocktails are dished out by no-nonsense bartenders in this perfectly maintained turn of the century bar. This is a spot is for listeners — you will get shushed if you get too loud. Come to the neighborhood a couple hours before your show to lose yourself in some of the city’s best Ethiopian food at Demera, which is across the street.
Noble Square
If you take a cab here, don’t get scared when your driver turns into what seems like a parking lot for garbage trucks. This dive occupies a weird and lonely corner of the city, but once you walk inside, it’ll all make sense. Good beers, friendly staff, and a great room in back for live shows. They do a lot here: concerts, theater, discussions and interviews, comedy shows, etc. If you’re not sure where to start, Devil in a Woodpile’s weekly shows are back and always worth it.
