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The Perfect Chicago Weekend Itinerary - Crafted by a Local!

A local's guide to a perfect three-day weekend in the Windy City.

the Willis tower viewed from Grant Park

Welcome to Chicago! Whatever you want to call her, the Windy City, the Second City... she’s an exquisite place to visit and to call home. I’ve been a Chicago native for almost eight years, and I’m constantly discovering new things about this glorious town I call home.

There’s far more to Chicago than you’ll be able to see in one weekend, or even in one lifetime. But if you’re in town just for the weekend, here’s a local’s recommendations on how to hit all the highlights!

Day 1: Get Acquainted!

Arrival and Check in

It’s Friday afternoon, and your plane has just landed at O’Hare or Midway. (Unless you drove in from a nearby state! Lucky you!) You collect your luggage and head for the doors.

Your first order of business will be to get yourself downtown. If you’re the adventurous type who’s down with public transit, the CTA (Chicago Transit Authority) is the most cost-effective way to reach the city center. O’Hare sits on the end of the Blue Line, and Midway sits on the end of the Orange Line. You can buy tickets right at the station from the rows of kiosks. If you’re in town for the weekend, I recommend the 3-day unlimited ride pass! If you’re not the type to take the train or just want to get into town a little faster, Uber and Lyft both operate in Chicago.

Afternoon - River Tour

A river tour is a great way to get acquainted with the sights of the Loop. Here are your two best options!

The first is to book an Architecture Cruise. There are several companies that offer river tours that depart from the docks near Michigan Avenue. The Architecture cruises feature a knowledgeable guide that will spend the cruise telling you stories and factoids about the city, its buildings, and the history involved with both. The tours will go on rain or shine, so dress for the weather and pack sunscreen in the summer! I can personally vouch for Wendella Cruises (ask me about the time I chaperoned two dozen drunk architects on an architecture tour!), but Shoreline Excursions also comes well reviewed.

The second option, for a more hands-on approach to the river, you can book a kayak tour! There are two major kayak tour companies, and I highly recommend Chicago Waterriders. Their launch point is a little further away, but they are the far superior tour company. Your ticket includes a brief kayak lesson and a guided paddle with a skilled team of river guides.

Regardless of your choice of boat, a river tour is a great way to see spectacular views of the city on your first night in town.

Evening - Dinner on the Riverwalk

The City of Chicago has done a truly remarkable amount of work on its Riverwalk in recent years. (Did your river tour guide tell you the story about Dave Matthews and his tour bus? Ask your river guide about Dave Matthews and his tour bus!) What this means for you is that the south bank of the Chicago river has become a gorgeously manicured trail of walkways, public spaces, and restaurants. Now that you’ve worked up an appetite on the river, it’s time to grab a seat on the edge of the water for some dinner.

You can find a wide variety of restaurants facing the water, but my top recommendation is The Northman on the River. This restaurant and cider house specializes in, of course, cider, as well as beer and bohemian food with a creative twist. I would swear by their House Cider and the curried chicken salad sandwich. And if you’re visiting in the summer, there will likely be live music under the shelter!

Cloud Gate "the Bean" after dark

Night - Visit the Bean

Quick disclaimer: I wouldn’t recommend this walk alone after nightfall. But if you’re in a group, the absolute best time to visit the infamous Bean is after dark!

Officially called Cloud Gate, “the Bean” is the famous reflective statue situated in Millennium Park. During the day, it’s surrounded by selfie-taking tourists all jostling for their perfect reflective spot. In the height of tourist season it’s never empty at the Bean, but after dark the crowds thin out, and seeing all the city lights reflected in its surface is really something else.

Day 2: A Full Day of Experiences

Morning - A Big Breakfast

It’s Saturday morning on your busiest day in Chicago, so it’s time to fuel up with a breakfast of champions. You can throw a stick and hit a brunch place in the Near North Side, but my absolute favorite place for breakfast in the city is a place that specializes in it: Yolk.

Yolk has several locations across the loop and the near north side, and the same spectacular menu is available at all of them. Yolk has a little bit of everything, and the portions are definitely sharable. My main dish of choice at Yolk rotates every time I visit (there’s way too many good ones to have a ‘usual’), but I nearly always accompany that main dish with a glass of Horchata Cold Brew and a single slice of the Very Berry French Toast.

Late Morning and Early Afternoon - Museum Visit

Chicago’s sprawling Museum Campus is absolutely world class and has something for everyone. The main museum campus is home to the Shedd Aquarium, the Field Museum, and the Adler Planetarium. Off the main campus but still in the Loop is the Art Institute of Chicago. For a short trip like the one you’re on, I recommend picking one and giving it the time it deserves! Let me help you pick one:

The Shedd Aquarium: massive, multi-level aquarium with galleries upon galleries of fish, tanks full of dolphins and beluga whales, penguins, and river creatures like otters.

The Field Museum: The Field is Chicago’s natural history museum. Think dinosaurs, mummies, and artifacts from global cultures. My personal favorites are the Ancient Americas exhibit and the newly redesigned Native American culture exhibits.

The Adler Planetarium: The Adler is a much smaller museum, and very wordy. If you’re visiting the Adler, you need to be in the mood to do a LOT of reading about space. But the artifacts on display are cool and the view of the Chicago skyline from the grounds is unparalleled.

The Art Institute of Chicago: A truly exquisite art museum with enough galleries to spend a lifetime exploring. Hit the impressionist galleries for the most famous pieces in the museum, but don’t sleep on the Arts of the Americas section at the back, or the international galleries scattered throughout.

Afternoon - Magnificent Mile Stroll and Lunch

Unless you’re a real shop-till-you-drop kind of person, I don’t actually recommend spending much time on the Magnificent Mile. But once you’re all museum-ed out (I usually last 2-3 hours in a museum myself…) the Mag Mile makes for a beautiful stroll to your next destination, as well a great place to grab lunch! You can find all varieties of fast food, or you can grab a seat at one of my favorites:

For counter serve burgers and killer shakes: Shake Shack

For delicious chicken with a spicy twist: Nando's Peri Peri

For upscale pub food and craft beer: Crushed by Giants Brewing

For admittedly pricy but authentic Italian food: the first floor counters at Eataly

For a sugar boost: Stan’s Donuts

Late Afternoon and Evening - The Signature Lounge and Luxbar

You may have noticed that the Sears/Willis tower is not in this itinerary. That’s on purpose. The best views of the city come from the Signature Lounge in the Hancock Tower, at the north end of the Magnificent Mile. The top floors of this building are a lounge and a restaurant with views of downtown that are just to die for.

If you want to eat at the restaurant, you’ll need to make a reservation months in advance and be prepared to fork over a few hundred dollars for the bill. That’s why I recommend the lounge! There will likely be a line for the elevators, but if you visit in mid-to-late afternoon, that line will move pretty quickly. And when you get to the top, you get to sip a drink at a table with the best views in town. Is that drink a little overpriced? Of course, but it’s less expensive than your ticket to get to the top of that other tower, and you get a drink out of the deal!

After your drinks with a view, it’ll be time for dinner. There are dozens of exquisite restaurants in the area, but my personal absolute favorite is Luxbar. Everything on their menu is excellent, but my usual there is the Build-Your-Own Manhattan (they give you a little menu to make your whisky and mixer selections), and the Steak Frites. I’ve eaten steak frites in Paris. The steak frites at Luxbar are better. Get them with a side of garlic aioli and bask in the deliciousness.

Day 3: One More Wild Adventure for your Chicago Weekend Itinerary!

Morning - A Divine Breakfast

It’s Sunday, and it’s your last day in Chicago! For your final breakfast, take the crew over to The Goddess and the Baker. This beautiful bakery and cafe has breakfast options for days, pastry cases full of tempting treats, and literally dozens of specialty coffee drinks to choose from. (My favorite is the wildflower honey latte!) As an added bonus, they’re super queer friendly and are nearly always serving slices of rainbow cake! Maybe order a few extra pastries to go and take them with you to your next destination.

a child pointing at a monkey at the Lincoln Park Zoo in Chicago

Late Morning and Afternoon -

The Lincoln Park Zoo

With breakfast under your belt, it’s time to make tracks for Chicago’s most amazing free attraction: the Lincoln Park Zoo!

Yes, the Lincoln Park Zoo is completely free to visit. It boasts 49 acres and hundreds of different animal species, from penguins, to gorillas, to giraffes, to lions, and everything in between. Is the weather a little dodgy? No worries! There are half a dozen buildings housing small mammals, reptiles, African creatures, primates, birds, and more. You will easily spend a few hours taking in the exhibits, and the free admission makes it very easy to justify that giant pretzel or the stuffed snow leopard from the gift shop.

Lunch - the Bourgeois Pig Cafe

If you leave the zoo with enough time to grab lunch before your flight home, you can’t do better than the Bourgeois Pig Cafe. It’s home to one of my favorite coffee drinks in the city: the Cafe Miel, a honey-sweetened latte with cinnamon. And for lunch, they have a huge menu of creative sandwiches, most of them named after literary classics. It'll be an excellent, hearty lunch to keep you caffeinated and full for your trip back home.


I hope you enjoy your visit to Chicago! Hopefully this weekend itinerary has whetted your appetite for this beautiful city, and we’ll see you again and again for years to come!

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Love and Shenanigans,


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