When I first moved to Chicago, I moved to the heart of the city’s tourist district, The Loop. I did all the classic touristy stuff and — trust me — some of it isn’t worth seeing. Now when my friends come in town, I recommend a mix of can’t miss tourist spots and local favorites. I finally compiled all my recommendations into my weekend guide to Chicago.
The Ultimate Weekend Guide to Chicago
There are three things every first timer to Chicago needs to see: The Bean, the lake, and the skyline. The Bean (whose official name is Cloud Gate) is the icon of the city. The massive lake looks like the ocean and even has a beach. And the architecture is some of the best in the world.
Day 1: Chicago’s Signature Icons
Start at Millennium Park for a selfie at the Bean so you can prove to your Instagram followers that you are, in fact, in Chicago. From here, you have a few choices to check out the lake and the skyline.
Go Touristy: Magnificent Mile & the Hancock
After your Bean selfie, head north on Michigan Avenue towards the building formerly known as the Hancock Tower. (Locals will forever call it that no matter what it’s renamed.) Shop your way up the Magnificent Mile, but don’t be surprised when you realize the famous shopping street is filled with the same stores as your local mall. Yep, the Mag Mile is pretty overrated, so don’t say I didn’t warn you.
Moving on. Once you reach the Hancock Tower, head to the Signature Lounge at the 96th floor for the best view in the city and an overpriced cocktail. Or you can pay for a tour of the top and have a drink at Bar 94 at the 360 Hancock. Yes, it’s touristy. Yes, you’ll have to wait in line for the elevator and they shove enough people in it to make you need a cocktail at the top, but the views are worth it. (As long as it’s a clear day! If not, stay street level.)
Go Local: Rooftop Cocktails
If drinks with a view are your thing but throngs of tourists aren’t, hit a rooftop bar for a view without the price tag. Cindy’s, on the top floor of the Chicago Athletic Association Hotel, has an awesome view of Millennium Park and the lake. London House, on the other hand, has an unbeatable view of the Chicago River from the 22nd floor. Expect crowds and expensive cocktails, but significantly less tourists than the Signature Lounge and no entrance fees.
Take a Boat Tour
After you’re nice and dizzy from a cocktail and an elevator that flies up nearly 100 floors at 20 mph, make your way to the river for an architecture boat tour. It’s the best way to learn about Chicago, its history, and its architecture. It’s the best thing to do in the city and a guilty pleasure of mine.
Several companies have boat tours, so the one you choose depends on what you want to see. Some focus just on architecture or the river, while others do the river and the lake. Here are all Chicago architecture tours with prices.
What to Skip
Don’t waste your time at Navy Pier — it’s just touristy fluff. Seriously, there’s a damn Margaritaville there! And even though the Sears Tower — officially the Willis Tower to everyone who doesn’t live here — is the tallest building in the city (for now), the views at the Hancock are still better. Unless you’re doing yoga on the 103rd floor.
Taste Chicago’s Signature Foods
Your first day is all about covering Chicago’s basics. Of course that includes Chicago’s iconic foods: deep dish pizza and a Chicago hot dog. For lunch, make a quick stop at Portillo’s for a hot dog. Or have a classic Italian Beef sandwich, dipped. (Portillo’s chocolate cake is worth it too!)
For dinner head to Lou Malnati’s, Giordano’s, Pequod’s or any of the deep dish chains scattered throughout River North. It doesn’t matter which one you pick, all of them are hotly debated so they all allow you to join the conversation.
Music of the Night
The 1920s made Chicago notorious for three things: speakeasy bars, gangster crime, and jazz clubs. And come to think of it, we’re still known for good bars, crime, and music. Andy’s and Jazz Showcase have intimate vibes and play live jazz every night. The Bassment has a more club-like atmosphere and Kingston Mines serves barbecue to a lively crowd.
Day 2: Explore Chicago’s Specialties
Start day 2 by waking up your sweet tooth. Donuts are ultra popular in Chicago so shops are everywhere. Stan’s Donuts is the crowd favorite, followed by Glazed and Infused and Do-Rite, but supposedly the best is Doughnut Vault.
The closet-sized shop is so popular, lines form down the block hours before opening and — I hate to admit this — the donuts are actually worth the wait. There’s no place to enjoy them there, so grab them and head to the riverwalk to enjoy them.
Nerd Out at a Museum
Chicago is home to some of the best museums in the world. And with dozens of museums, there’s one to indulge your interest. The Art Institute is a local and tourist favorite — it was voted a top museum in the world on TripAdvisor 5 years in a row — with art spanning ancient cultures to contemporary. (And, of course, that one from Ferris Bueller.)
There’s also the Field Museum for natural history nerds, the Museum of Contemporary Art for abstract lovers, the Adler Planetarium for science geeks, and the Chicago History Museum to learn about the city’s nitty gritty past. Animal lovers have a tough pick between the Shedd Aquarium and the Lincoln Park Zoo, but remember the zoo is free.
Sound of Music (or Laughter)
Since you’re visiting in the summer (let’s face it, no one comes to Chicago in the winter), there are free concerts at Millennium Park. And the best part, besides being free? They are BYOB. So stop at Eataly or Pastoral for wine and cheese, find a blanket, and enjoy the show.
If you do happen to find yourself in Chicago’s arctic tundra, check the schedules for the Chicago Symphony Orchestra, the Lyric Opera in the stunning Civic Opera House, the Joffrey Ballet, and Broadway in Chicago. There are dozens of theaters showing Broadway’s best hits. Or see comedy at Second City, famous for incubating stars like Bill Murray, Tina Fey, Steve Carell, and Stephen Colbert.
Day 3: Live Like the Locals
In Chicago, we like to drink. So start with brunch like the locals: a noon reservation and bottomless mimosas. Opt for chicken and waffles at Miss Ricky’s, get fancy at 3 Arts Cafe, or focus on food at Regards to Edith.
Lakeshore Pride
Speaking of Chicago’s arctic tundra, once that finally melts away we love to be outside. (Have you noticed how every sidewalk is taken over by seating?) And the lake is one of our favorite outdoor spots. If you know someone with a boat, head to the water (and give them my number!). Otherwise, bike along the lakeshore path on a Divvy bike (Chicago’s bike share program), hang out at the beach (yes, we have an actual beach with actual sand) or go for a walk along the water.
If all else fails, partake in my favorite outdoor activity: drinking outside on one of the many patios or rooftop bars. Apogee, Raised at the Renaissance, Joy District, Big Star, and Rock Bottom have great patios.
Play Ball!
Even the most mediocre of sports fans knows Chicago sports are not to be messed with. Even those sports where we don’t exactly dominate, the crowds are infamously full. So no matter your sports — baseball, basketball, hockey, football, and soccer — we have a team.
But Chicago loves baseball. We have two teams with a rowdy rivalry between them. Head to the north side for the iconic Wrigley Field, one of the oldest in the country, to cheer on the Cubs alongside a wild crowd. Or go south to the worst named stadium in the country (Guaranteed Rate Field) for a relaxing Sox game with better food, less rowdy fans, and cheaper tickets. The Red Line on the L takes you to both!
Foodie City
Chicago is one of the best food cities in the country, if not the world. Needless to say there are a ton of good restaurants here but getting into the famous ones isn’t always easy.
Au Cheval supposedly has the best burger in the country but be prepared for a 2-5 hour wait. Purple Pig, a touristy favorite, isn’t worth the wait considering the number of amazing restaurants just blocks away. And you’ll probably have to book your trip around reservations for Alinea or Next (seriously).
My recommendations: Tanta for Peruvian-Asian fusion, Monteverde for Italian, Mercat a la Planxa for Spanish tapas, Ramen-San for ramen, Momotaro for Japanese, Table Donkey and Stick for Eastern European, and Crisp for Korean fried chicken. (Here’s why.) Other sure picks: Big Star, Wrigley BBQ or Chicago q, Blackbird, and Bad Hunter.
That’s right: I’m telling you to skip Girl and the Goat and Duck Duck Goat, Stephanie Izard’s popular spots, and Ricky Bayless’ Frontera Grill (but definitely go to Xoco for the Cubano!).
Cheers to Chicago
And, finally, end your evening with drinks. To figure out where to drink to Chicago, that requires its own entire article. Here’s where to drink in Chicago based on what drink you like. With hundreds of bars in the city, it really requires its own post!
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There you have it: my weekend guide to Chicago. What did I miss? Let me know the Chicago favorites I missed in the comments. Cheers!
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Great work Kelli. I see a few things on here we will tackle. Can’t wait GO UTES
Can’t wait to have you all here! GO UTES!