A while back, a reader asked me if I would write up a guide to visiting Chicago. I obviously was happy to, but it's taken a while to get it together because I didn't want to half-ass it. If I'm going to whole-ass anything, it's going to be this. Chicago may be the size of one borough of New York, with none of the ocean views of Los Angeles or the mountain views of Seattle and Portland, and our winters are fucking brutal and our mayor has his head up his ass and all our governors are in jail, and somehow I still love it here more than anywhere else.
This post is going to be looooooooooong, so get cozy. I wanted to try and span the city a bit, and not just focus on my neighborhood (Logan Square, though many of these options are in and around my 'hood), drum up not only my favorite restaurants and bars, but great shops and venues and museums and and sightseeing, spanning all budgets (okay, not all budgets because I don't know how to be a rich person in Chicago). This list is not comprehensive, or perfect, and I left some places off that I always go to (because they are boring but centrally located for me and my friends) or because I know they're supposed to be awesome, but I haven't actually been yet (lookin at you, Au Cheval). Without further ado, let's get started! All lists are in no particular order, but FAVORITE-favorites are noted in red. And remember, when I say "Best", I really just mean "Meg Zandi's Favorite", it's just easier to type.
Best Brunch Places
Best High-End Restaurants
Best Pizza Places
Best Independent Shopping
Best Downtown Activities
Best Free Activities
Overrated Chicago Tourist Suggestions
Assorted Tips and Tricks
Best Brunch PlacesThere is a list of bars further down the page, so I figured you'd need brunch options too. Chicago is a big brunch city, but that doesn't mean always waiting in long lines to overpay.
Windy City Cafe (River West) - This place isn't much different than any other greasy spoon diner, but in a town where brunch lines can be two hours long, it's a nice respite. It's never crowded, but always solid. Right off public transit and the expressway, between "hip" neighborhoods and downtown the service is good, the food is cheap, and it provides a good base fuel for the day if you don't want to waste too much time on breakfast. And they always give you a cup of coffee to go for no extra charge!
Flying Saucer (Humboldt Park) - This cash-only joint has some quirks, like you have to ask for ice in your water, and the service sometimes leaves something to be desired, but if you have dietary restrictions (vegan, gluten-free, etc) and still want a satisfying brunch, this is where to go. Get the breakfast bowls, they're awesome.
Lula Cafe (Logan Square) - No brunch list is complete without Lula. This place will always have a bit of a weekend wait, but its always worth it. It's not just a place to fuel up, it's an excellent farm-to-table style meal. The food is ~artisanal~ and kind of fancy, but the space is low-key, the prices are not unreasonable, and the portions are perfect. I wouldn't recommend going with any more than 4 people though - the smaller your party, the shorter your wait.
Dunlays on the Square (Logan Square) - If the line at Lula is unbearably long, head around the corner to Dunlays. It looks lame from the outside, almost like a chain restaurant, but its pleasantly surprising inside. There is never a wait, the bloody mary's are great, and the fried-chicken-and-waffles eggs benedict is the thing dreams and heart attacks are made of.
Siena Tavern (River North) - I don't normally venture to River North, since its kind of yuppie and ritzy, and by that I mean that people actually shower before going to brunch. Siena Tavern is definitely worth a mention though because not only is it delicious, but it's close to most of the hotels tourists stay in, and much closer to the museums, the lake, the whole downtown area than the other places mentioned. Unlike most brunch spots, Siena does accept reservations and can handle larger parties.
Tre Kroner (North Park) - I don't see the far-north neighborhood of North Park on a lot of Chicago visit lists, but this is definitely worth going out of your way a little bit. Again, its a place to go with a smaller party and plan for a wait, but the traditional Swedish breakfast is unique and delicious, with the highlight being their sweeter options (pancakes, waffles). No alcohol though, so don't go here if you need a hair of the dog.
Bang Bang Pie Shop (Logan Square) - Bang Bang's biscuits with butter sit atop a list of my three favorite meals in Chicago; this is the best breakfast you'll ever have. It's casual, with a small menu of just pie and biscuits, but its PERFECT, you'll never have better anywhere else. Mark my words. This place also has the added bonus of probably seeing me there, since I go at least once a week in the warmer months (space is limited inside, but they have a huge yard.)
Jesus, this post is already a million words and I'm only done with brunch. I'll try to be a bit more brief with these restaurant recs. Again, in no particular order...
With a focus on casual and affordable spots to stop for lunch or dinner.
Big Star (Wicker Park) - in the heart of a neighborhood with tons to do, my favorite tacos in the city. Definitely get the al pastor, the fish tacos, and a Michelada. Plan for a wait, for sure, or hit up the cash-only takeout window and eat it in the park next door.
Little Goat (West Loop) - the casual, diner-style sister of Top Chef winner Stephanie Izard's Girl and the Goat, its easier to get a table, huge portions, unique takes on diner food, and a photobooth while you wait. Get the mac and cheese, the crab dip, and the cheez-it gelato (yes, really).
Black Dog Gelato (Wicker Park and Roscoe Village) - If you have a sweet tooth, you need to go here. Thick, creamy, decadent gelato in flavors like goat cheese cashew caramel. So fucking good.
Hot Doug's (Avondale) - You show up super early for an outrageous line, and you wonder, why the fuck am I wasting my time on vacation in an hour-long line for hot dogs? IT'S SO MUCH MORE THAN THAT. This is possibly my favorite restaurant in the city. Known for creative dogs like alligator, foie gras, lamb, and snake, everything is rich and flavorful and perfect. Skip the duck fat fries, they are overrated and take up precious belly space. Ideally, agree to share with a friend so you can try more varieties. Two dogs will fill you up, three will make you want to die. Cash only.
90 Miles (Logan Square) - BYOB Cuban place, I always just let the waiter pick what I'm going to eat and its filling, delicious, leaves tons of leftovers, and costs like $12. Aim for the patio if it's open, and order the plantains.
Belly Shack (Logan Square) - Quick and easy meal if you're not looking for a big to-do. Get the Belly Dog (it has crunchy egg noodles and kim chee on it) and the sausage brussell sprouts.
Nuevo Leon (Pilsen) - BYOB Mexican. For $10 you will get more food than you could ever imagine eating, and it's all awesome.
Yuzu (West Town) - Best sushi in the city, hands down. Plan for a not-too-bad wait, go with only one or two other people.
Chicago Diner (Logan Square and Lakeview) - Best vegan food in the city, sure to please even hard core carnivores. Good beer list, my favorite menu items are the gyro and the milkshakes.
Calumet Fisheries (South Deering) - This place is a fucking hike, and you need a car not only to get there, but to eat in since there is no space to sit inside, but its so worth it. A million kinds of seafood, but make sure you get a mix of smoked and fried even though it's easy to order all fried. You'll even see a bunch of folks on the bridge outside with their fishing poles. Super no-frills, and get the hot sauce.
Lao Sze Chuan (Chinatown) - My favorite Chinese food spot. In the heart of Chinatown, great for groups so that you can share a hot pot: boiling broth for the table to cook raw meat and veggies in.
Pleasant House (Bridgeport) - Great comfort food for a rainy day. Crispy, flaky pot pies in a small and cozy byob shop. Stop in Maria's Packaged Goods next door before you head in and grab a six pack of Three Floyd's Zombie Dust, if you're lucky and it's in stock.
Jerry's Sandwiches (Wicker Park) - Throwing this one on even though its not particularly remarkable, it is just sandwiches done well, and there are literally a million menu combinations so it's good for when no one can decide what the fuck they want for lunch.
Ba Le (Uptown) - My favorite banh mi in a city where banh mi can be hit or miss. Lemongrass tofu is my favorite.
Tank Noodle (Uptown) - The pho here rounds out my top three favorite dishes in Chicago. Just driving by Tank Noodle makes me happy.
Rainbow Cone (Beverley) - Open from March to November, Rainbow cone is famous for a cone stacked with one scoop each of Chocolate, Strawberry, Palmer House, pistachio and Orange sherbet. Open since 1926, it is a Chicago institution.
Zaleski & Horvath (Hyde Park) - You'll hopefully make it down to Hyde Park to check out the museums, University of Chicago and to say hi to your old friends Barry and Michelle, and this sandwich shop is the perfect place to stop for lunch.
Higher End DiningChicago is establishing itself as a for-real food city, so stash away some dough for these pricier places. None of them are like, dress up fancy, but unlike the suggestions above, they will run you more than $50ish per person.
Girl and the Goat (West Loop) - Make your reservation as soon as you book your plane ticket, otherwise you won't get in. The cauliflower was incredible, the pig face was too much.
Blackbird (West Loop) - Go for the lunch prefixe to save $$$$ and get a good sampling of the menu. Sit on the patio if you can! (Worth mentioning - the waitress didn't make fun of me at all for not knowing how to pronounce any of their wines, even when I just ordered the second-cheapest one.)
Publican (West Loop) - Small plates to share, not one for the vegetarians. Best oysters I've ever had.
Nightwood (Pilsen) - Beautiful space, more of that farm-to-table style eating. Great cocktails, and again, not stellar for vegetarians, but doable. Good place to take your parents.
Best Pizza Places
Why yes, this does require it's own category.
Piece (Wicker Park) - The total opposite of Chicago-style pizza, this place goes for a New Haven-style big, flat pizza. I love getting mashed potatoes and/or clams on mine. They have an in-house brewery too, so try the house beers.
Dante's (Logan Square) - More big, thin slices. What can I say, deep dish is overrated. Get the Minotaur slice, skip the sides.
Boiler Room (Logan Square) - great vegan options, creative slices of the day, and a PBJ (pizza, beer, Jameson shot) will only run you $7. It's cash-only, but if you give them your atm receipt they will give you a free shot of whiskey for your troubles.
Pequod's (Lincoln Park) - if you must get deep dish, skip the big touristy chains like Lou Malnati's and Giordanos and head here.
Humboldt House (via Facebook)
Out-of-towners often get psyched to hit up stores that not every city has, like Zara, Topshop, H&M, but make sure to check out these local favorites too.
Humboldt House (Humboldt Park) - If you've been reading this blog for any stretch of time, you probably already know how much I love this vintage home shop. While it seems weird to visit a furniture store while on vacation, there are many carry-on friendly goods for sale, like their kilim pillow covers.
Quimby's (Wicker Park) - A great indie bookstore, perfect place to find local authors, graphic novels, zines, and souvenirs you will bring back and people will actually thank you for. Plus, there's a photobooth, which is always great.
Myopic (Wicker Park) - Yes, it's another bookstore, and yeah, its less than a mile from Quimby's, but it's floors and floors of new and used books at great prices. Great for finding plane reading or for dropping off your dad while you hit up some Wicker Park shopping.
Building Blocks (Wicker Park and Lincoln Park) - The best toy store in the city, it's a great stop if you're traveling with kids. I get all of my niece and nephews' toys here because I love the selection of classic toys, and the staff are the friendliest people on the planet.
Reckless Records (Wicker Park, Downtown, and Lakeview) and Logan Hardware (Logan Square) - my two favorite record stores. And hey, you can't feel too bad about buying records on vacation, they pack flat!
Inkling (Lakeview) - Another great souvenir shop. Great paper goods from local artists and big names like Rifle, affordable art, funky jewelry, excellent Chicago-centric gifts that aren't tacky.
Woolly Mammoth (Andersonville) - A shop of oddities, ranging from taxidermy to antique medical supplies to vintage school maps. There's nowhere else like this place.
Best Thrifting - Family Thrift on Milwaukee and Francis, Village Thrift on Milwaukee and Armitage, Unique Thrift on Kimball.
Low-key places for cheap beers and/or fancy cocktails
Scofflaw (Logan Square) - Come for the gin cocktails, stay for the decor and the fancy bar snacks.
Whistler (Logan Square) - Cocktails that sound ridiculous, taste amazing, and cost $8. Sit on the patio out back, prepare for crowds, check out the rotating art installation in the window.
Skylark (Pilsen) - Huge, dark, cheap beer, laid-back crowd, old-school photobooth.
Green Eye (Logan Square) - Big space, board games, nice IPA selection, relaxed atmosphere, no one trying to look too cool.
Guthrie's Tavern (Lakeview) - Okay, I've only been here once, but I loved it and figured I needed to give you some options further east. It feels like you're drinking at someone's grandma's house, with Christmas lights and board games and cheap drafts and I love it.
Gingerman (Wrigleyville) - I hate Wrigleyville, but if someone makes you go see Wrigley Field or some shit, this is a good bar to make it worth your while.
Dorothy's / Go Liquors (Logan Square) - Just a door or two down from Scofflaw, it's a good place to go if Scofflaw is too crowded. Super laid back, bartenders that will stroke your ego by telling you you're pretty, insanely cheap pulls of really good beer. Good selection of beer to go.
Fischman's Liquors and Tavern (Jefferson Park) - This feels like your dad's favorite bar. The seating is ample, not a hipster to be found, the game will always be on, and the service is always quick and friendly. Try and go on a night where they do a tapping to get a taste of more rare beers, especially because a bunch of food trucks always roll up outside. (On these nights, the no-hipsters thing no longer stands.)
Favorite bars for beer geeks - Map Room (Logan Square), Hopleaf (Andersonville), and Goose Island and Half Acre for brewery tours. Honorable Mentions for Three Floyds and Flossmoor Station, both of which are about a 30-45 minute drive out of the city.
Can't spend another night drinking and eating deep dish? Get some culture, you philistine.Empty Bottle (Ukrainian Village) - Small venue but never feels cramped, excellent bartenders, great sound and sight lines, and of course, a photobooth.
Hideout (Noble Square) - Go on Mondays to see folk / country artist in residence, Robbie Fulks who not only puts on a great show, but is great for banter between songs as well.
Honorable mentions - Wednesday night jazz at Lilly's in Lincoln Park for the laid-back but upbeat, and any night jazz at the Green Mill in Uptown for a more serious jazz experience in a historic venue with an awesome classic neon sign. I don't love the Green Mill as much as everyone else, but it is cool inside and parents seem to love going there, so there's that. Don't forget about Chicago's improv scene as well, with Second City being the standout.
The Art Institute, via
This is a category where I feel like the reminder that "best" just means "my favorite" is important to note!
Museum of Science and Industry (Hyde Park) - All of our museums are great, but this is the best one, hands-down. Everything in it is fucking awesome, it makes you feel like a kid getting their mind blown in science class again. Great for adults and kids.
Art Institute of Chicago (Downtown) - This has been my favorite art museum since I was a kid, but the addition of the Modern Wing really took it over the top for me. Relive scenes from Ferris Bueller in the Impressionist wing and make sure to check out the elaborately detailed miniature Thorne Rooms. The attached restaurant, while expensive, is also delicious and has amazing views. Even if you don't eat at the restaurant, make sure to walk across the bridge connecting the museum to Millennium Park to catch great park and lake views.
Best Downtown Activities
Chicago is a city of neighborhoods, and I always try to urge people to get out and explore them, but I admit no touristy trip to Chicago is complete without a stop in the heart of the city. You can be a tourist, just be a good one.
Millennium Park - I admit it, I fucking love the Bean. It's so cool looking, and it never gets old to me. You'll have a million other tourists in all your pictures (unless you try this cool trick), but its really no big deal. There are also these two giant fountains, Crown Fountains, that are interactive brick video sculptures over 50 feet tall that project images of Chicagoan's faces. If you hang out long enough, these sculptures will spit on you. I'm not kidding. The Millennium Park amphitheater is a design marvel, so don't forget to peek at that too.
Chicago Architecture Foundation Boat Tours- In my opinion, there is no better way to see the city. Its a tour boat that takes you down the river, where a gregarious and charming guide gives you a history of all the architecture, and then you loop back out onto the lake for sightseeing (just make sure to buy tickets for the River AND Lake tour, not the one that's just the River tour). There's a bar on deck, photos are encouraged, and the views are unrivaled. A great option if this is out of budget is to take the Chinatown water taxi. It's a similar route, but is only $4.
Michigan Avenue - Is it touristy? Yes. Is it pretty? Yes. Are there a fuckton of stores? Yes. You have to be patient, up for doing a lot of walking, and like shopping, but if those things float your boat, the Magnificent Mile is admittedly a cool thing to check out if you're new in town. It ends at the original Water Tower, which sometimes has cool art installations in it.
Hancock Center - You can do this two ways: you can pay for admission to the Observatory for panoramic views of the city and space to wander, or you can skip the admission fee and get similar views in the Signature Room bar. The views here are better than from the Sears (ugh, Willis) Tower, even if they don't have the invisible ledges that hang over the city.
Oak Street Beach - Get great views of the city while also having a full beach experience. Don't forget to check out the murals on the pedestrian walkway, and be sure to look both ways before crossing the bike path.
Downtown bars that aren't terrible: Skyride (dive bar), The Berghoff (first liquor license in Chicago!),
Best Free Activities:
Because you bought too many specialty cocktails at the Whistler last night.
Chicago Cultural Center (Loop) - The architecture of the building itself is beautiful, and the contents make it even better. The rotating art exhibits are always free and never lame. The grand ballrooms are ornate and magical, and it is home to the world's largest Tiffany's dome.
Concerts in Millennium Park (Loop) - These happen all throughout the summer, and everyone packs up picnics and bottles of wine to lay in the grass and listen to music.
North Park Village Nature Center (North Park) - This forest preserve in the city is great for decompressing and walking around. Also, you are guaranteed to see a fuckton of deer, which scared the shit out of me the first time I saw them.
Montrose Beach (Uptown) - This is my favorite beach in Chicago. While the views aren't as good, they are still pretty solid, and this beach doesn't get as crowded as the others. It's also home to one of the city's dog beaches, so you can swim surrounded by tons of puppies, which is a dream I have nightly. Montrose Beach is also home to Cricket Hill, where on a warm and windy day, tons of people will be flying kites, which is at once surreal and beautiful.
The Boulevards (Logan Square) - There are several boulevard districts in Chicago, but of course the ones in Logan are my favorite. These thick patches of grass are perfect for picnics, grilling, frisbee, just general lazing. On Sundays, the Logan Square farmers market takes over the boulevard with plenty of ready-made food options for your picnickin' needs.
Garfield Park Conservatory (Garfield Park) - Rooms upon rooms of lush greenery, exotic plants and beautiful flowers. It's the perfect place to just zen out for a few hours, take some bitchin' Instagrams and find a nice counter to the concrete cityscapes.
Free Museum Days - Chicago museums almost all have one free day a week, which is a great way to explore. Aside from the ones listed above, I'd check out the Shedd Aquarium, the Planetarium, The Museum of Contemporary Art, and the Field Museum, in that order.
Overrated Chicago Tourist Suggestions
Not that there is anything inherently wrong with liking these places, I just think you can use your time at more affordable/cooler/tastier/less lame places.
- Lincoln Park Zoo - Its just sad.
- Ed Debevics - The schtick isn't worth the shitty food
- Glazed and Infused / Donut Vault - I love when other people buy them for me, but I don't love sweet breakfasts or long lines early in the morning for places that don't even serve bloody marys.
- Wiener Circle - How did this place get so famous it's the fucking worst
- Clarke's Diner - A Chicago staple, maybe, but its probably just going to be full of drunk high schoolers. Take it from someone who spent a lot of high school drunk at Clarke's.
- Billy Goat Tavern - You will pay $26 for a cheezborger just because this place is ~famous~.
- Reno - This might not be overrated yet, but I keep seeing it pop up on otherwise good lists, and its a total waste of time and money. Everything is cooked wrong and they'll fuck up your order after making you wait 45 minutes for a bagel.
- Wrigley Field - Go to Comiskey and see a real baseball game.
Things That Didn't Fit Anywhere Else in This Post-
- Download a taxi app like Hail-O or Uber before visiting. Chicago cabs are required to take credit cards, but they sometimes fight you on it, and it can be difficult to hail a cab if you aren't in Lakeview or the loop. These apps bring the cab to you and bill directly to your credit card.
- That being said, use the CTA! It's cheap and easy to get the hang of. I'm of the opinion that you haven't really experienced a city until you've experienced it on public transit.
- To avoid expensive downtown hotels or inconvenient airport hotels, look at AirBnb or try to snag a room at Longman and Eagle. (Bonus: if you stay at Longman, you get priority seating at the restaurant!)
- If you're from somewhere that doesn't get a lot of smaller-release movies, the Century Landmark on Clark and Broadway always has the best selection of films, with a focus on limited-release movies.
- Don't be afraid to ask for directions or suggestions. I don't know if Chicago has a reputation for being unfriendly the way that New York does (which I don't even know if that's true), but everyone I've ever seen is happy to help.
- If you have more than 500 followers on Instagram, download the Popular Pays app. In exchange for your social media capital, you get free shit all over the city, including a few places on this list!
- Drink the Malort. Just do it.
Taken on Wendella Boat Tour
PHEW. Well, I hope that was helpful and didn't just overwhelm the fuck out of you. If you have any questions, ask them here! I'd love nothing more than to keep talking Chicago, since I'm a little sad this post is now over.