Chicago is one of the best cities in the country…nay, the world, to visit. An epicenter of food, culture, art, sport, and architecture–it has it all. I’ve been to the Windy City at least a dozen times (and I’m heading back there this weekend), and undoubtedly, I’ve had some of the best times of my life there. This guide is my ideal time in the city, but there’s no humanly way possible you can eat to your heart’s content in such a short period of time. But no one will hold it against you for trying.
Do you remember when? Fireworks at Lake Michigan, cuz I’m coming home again –‘Ye
Hit the ground running when you get to Chicago on what is presumably still a weekday, and get yourself a light breakfast. The Eastman Egg is a hipster food-truck turned brick and mortar with local meat and egg sandos. Their coffee is also pretty good.
I picked this slightly off the beaten path location in the West Loop to start your adventure because it’s a few blocks away from Willis Tower (aka Sears Tower).
At least once in your life, should you visit this formerly tallest building in the world and experience the 360 views of the city 📷.
The glass walkways that jut out over the side of the building are terrifying but provides an unparalleled view of this grand city.
You’ve earned a hearty lunch and Xoco is just the place. Xoco is one of celebrated chef, Rick Bayless’s more casual eateries (joining Frontera and Topolobampo) and there’s a reason why he’s trained scores of famous chefs in their own rites. Xoco is bomb. As in, the tortas are crispy, gooey flavor bombs. I dream about the Milanesa. Don’t skimp out on dessert, they have churros and bean-to-cup pure drinking chocolate.
Now you’re ready to take on the art world at The Art Institute of Chicago. If you’ve never been here, you have to go. This is one of the best museums in the world with recognizable work after recognizable work.
The Art Institute ($25 for non residents, $20 for Chicagoans) is located in Millennium Park, at the north end of Grant Park, very close to Anish Kapoor’s Bean at Cloud Gate 9. This is a must see icon of Chicago 📷.
Also check out the Frank Gehry designed Pritzker Pavilion, a bandshell just yards away. On the weekends there’s yoga in this area of the park too, which looks like a great way to assimilate with the locals. I’m usually busy eating, but next time!
Hike north of the Loop to the river towards Michigan Avenue. The Chicago River runs right through the city, and is as much of a landmark as any other famous building or structure. The DuSable bridge will take you across this large expanse of water to the glorious mecca of shopping/dining that awaits you on the other side. On St. Patrick’s weekend, the river is dyed green–if you get a chance to see this, take it, it’s awesome.
The famous and not to be missed architectural tour leaves from the north side of the bridge and leads tourists and natives alike through the maze of skyscrapers like the Tribune Building for which this metropolis is known:$46 for daytime, $49 twilight cruise.
Spend the rest of your afternoon shopping to your heart’s content at the the shops in Michigan Avenue’s Magnificent Mile. Keep your eyes peeled for the John Hancock building, in which there’s a great observatory/The Signature Room where you can have a nice pre-dinner drink.
Do not forget to visit Chicago’s landmark Garrett Popcorn–get the Chicago mix cheddar and caramel. It will change your life. You’ll never be able to look at popcorn the same way again.
There are so many options for dining, you can spend hours debating where you should go. So come with a game plan depending on where your night is going to take you.
If plans are in the air, maybe something casual like pizza. Lou Malnati’s. There’s probably a debate on what is better: Giordano’s or Lou’s, and well, there shouldn’t be because Lou’s is the best. There’s multiple locations all over town. If you’re looking for a different take on pizza, or you’re going out in Wicker Park later, Piece serves extra thin crust New Haven style. Their brews are killer, too.
Looking for more upscale? RPM Italian serves old-fashioned family Italian comfort food in a chic settling. It’s down the block from some of the hottest clubs in town, so it’s super convenient. Definite a “scene” place, which can be fun.
You need to go out in Chicago. I don’t care if you’re old or think you’re too old, the nightlife in this city is probably my favorite. It’s amazing for people watching alone, but it’s easy to join in on the lasciviousness as well. This is probably the top town to go out in, because there are centralized areas and clubs that EVERYONE goes to. From the River North area of bottle service dance clubs, to rooftop bars which was teeming with “guys who work in finance” in the summers, to the more laid back and cool vibes of Lincoln Park, Wicker Park and Old Town.
Because you’ve had a casual dinner, you probably won’t be dressed to the nines, so head out to Lincoln Park, Humboldt Park or Old Town. These neighborhoods are filled with
bros casual pubs and taverns, but as with everything in Chicago, they’re all elevated. Pourhouse, Benchmark on Wells in Old Town are safe bets for good brews. There’s loads of hipster hole in the walls in Humboldt Park. Lincoln Park has a ton of Irish and English pubs like Lion Head, Red Lion and Galway Arms (be a Galway girl here). One of my favorite spots, the J Parker, sits on top of the remodeled Lincoln Hotel and it’s a nice respite from the downtown rooftop bar scene. Totally chill vibe.
There’s no experience to end your night of revelry and frivolity like getting a hot dog from Wiener Circle in Lincoln Park. This long time establishment is run by some saucy ladies who will sing and dance and yell at you in a NSFW fashion. It’s the best. And the greasy cheese fries hit the spot.
If you are like me and a night of drinking makes you get up extra early, I empathize. Fight through the fatigue with a donut like a champ. There’s lots of great choices in Chicago for donuts. Firecakes and Glazed & Infused on Hubbard (it’s fun to see it in a light of day and not filled with drunken revelers), Stan’s Donuts in Streeterville (an LA chain), and Doughnut Vault on Kinzie.
Go for a walk/run in Grant Park again (and don’t miss Agora, the moving Abakanowicz installation near Roosevelt and Michigan) and head past Soldier Field, home of Da Bears, to the shores of Lake Michigan. There’s a great concrete path where you can run and enjoy the panorama of the skyline as your backdrop. You’ll see the Field museum, the Shedd Aquarium, and if you travel far enough North you can see the Buckingham Fountain, famous for being in the opening of Married with Children and other sites.
If you’re not in the mood to get your endorphins going, and who could blame you, getting a massage at either the Peninsula or the W’s Bliss Spa is one of life’s great pleasures. The Peninsula in River North is architecturally stunning and provided me with one of the top 5 massages of my life. The Bliss Spa is located on the top floor of the W on Lakeshore facing the lake, so the view from their waiting room of the beach is stupendous.
Get lunch at Portillo’s. If there’s one thing you have to eat here, it’s a Chicago hot dog. Because I typically say in River North or the South Loop, the location on Ontario is the most convenient–and you get to drive by the rock ‘n’ roll McDonalds.
If the weather isn’t yet a million below, join the throngs of Chicagoans at the beach on Lake Michigan. Walk amongst the Gold Coast high rises to the North Avenue beach, were you can grab a day drink on the upper deck at Castaways. I’d skip Navy Pier, as there’s not much to see and is mostly full of tourists. But, there is a Giant Ferris Wheel which can offer you a unique view of the city.
Tonight, you should sample some of the upscale eats this city has to offer. Sunda on Hubbard is a sexy asian fusion hotspot, with melt-in-your-mouth crispy rice with tuna. It’s definitely a scene in which to be seen.
Or, if you’re high rolling, try to get a reservation from Alinea (or just get drinks at the Aviary in Fulton), Grant Achatz’s award winning establishment between Lincoln Park and Old Town. Probably the most celebrated chef in the city, which is saying a lot, he overcame head and neck cancer to return to helming one of the most successful restaurant empires in the country. He’s a gastronomic genius.
But if you weren’t able to score a coveted reservation, any restaurant in Fulton Market West Loop neighborhood is recommended. This neighborhood is so packed with eats that I suggest you come back for brunch tomorrow. Girl & the Goat is Stephanie Izard’s cinematic take on tapas featuring the protein in its name. Duck Duck Goat is her spin on Chinese. Every dish is inventive and savory.
Au Cheval turns casual food into a wholly upscale experience. Their burger. My god.
Chicago is not close to either coast, but that doesn’t mean you’re not going to experience some of the best sushi around. Momotaro has an extensive menu in a lounge, too cool for you setting. It’s very good. It’s all very good! There’s too many choices.
Because I am in my 30s, a lot of my 20s were spent on Hubbard Street. From Social to Hub 51, Hubbard Inn to Paris Club. There’s so much to drink and see, so little brain cells to kill. Around the corners are the Underground (Illinois) and Public House (Kinzie). All of these places may have waits, especially if you’re a man, and that can be brutal in the winy city’s frigid winters. These hotspots all are restaurants, but I couldn’t tell you any of the food that’s served there. I’ve been to all of the aforementioned places, but I can’t tell you the differences amongst them. Hubbard Inn has beautiful decor, Hub 51 has a basement with DJ and that’s about all I can discern.
We used to somehow also end up on Rush and Division at the most sketch, end-of-the-night-dregs clubs when we were young. Take it from me, just go home or go get something to eat.
Late night eats in Chicago can’t be beat and a big reason for that is Greek Town. Their diners are open way late and there’s nothing that hits the spot more than a gyro. Mr. Greek is open until 4 AM. I have had many gyros from here, it does not disappoint. It does give you heartburn, but pack some extra Tums. What were you expecting? It’s Chicago!
On your last day, take it easy and head to brunch. Again, any of the restaurants in the Fulton Market neighborhood (Fulton, Lake, Randolph Streets in particular) will tickle your taste buds and wake you up. Publican and Little Goat are new classics. The bacon at Publican is unreal, and I love that each booth has its own stable doors.
For the rest of the day, visit a neighborhood you haven’t been to yet. The South Loop/Theatre district and State Street in particular has a few notable Chicago landmarks like the Chicago theater with a Marina City tower 📷 . Perfect for your instagram.
Or head up to Wrigleyville, home of the Cubs. There’s a lot of sports bars around to watch any game from any sport, and Wrigley Field is definitely a historic landmark to behold, second to Fenway in age. Cubby Bear has a great atmosphere.
Before you head back home, I’ve saved the best for last. Kuma’s Corner is a heavy metal themed burger joint that has incredible burgers and mac and cheese. I am partial to the original location in Avondale, but now there’s a few locations around the city and in the suburbs. The Lair of the Minotaur, with brie, pancetta, caramelized onions and poached pears is a personal favorite. It doesn’t get more metal than brie and poached pears, let me tell you.
On your way out of town, marvel at the beauty of this Midwestern city’s skyline. It’s truly one of the best places to visit for a weekend or more. Just be sure to visit in the summer or late spring, early fall. It’s frickin freezing otherwise and you won’t have as pleasant of memories, although New Year’s Eve in Chicago is another story for another time.
Listen to: Smashing Pumpkins, Kanye, Chance the Rapper, Chicago, Sufjan Stevens’ Come on Feel the Illinoise! album, Styx, Wilco (see all their lyrics not so hidden in this post)
Must eat: Garrett Popcorn, Pizza, Chicago Dog
Sports: Bulls (NBA), Bears (NFL), White Sox & Cubs (MLB), Blackhawks (NHL), Fire (MLS)
Suggested souvenirs: Garrett popcorn, Nuts on Clark if you’re in MDW, sports stuff, the inevitable 20 pounds you just gained