How To Plan A Great Weekend In Chicago

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Chi-Town! Chi-Town! Chi-Town! A weekend in Chicago is the epitome of a good time. The city is such an icon and I’m pumped to help you plan a great weekend there. I mean I’m already drooling thinking about the ooey gooey deep-dish pizza, the iconic skyline, and all the amazing things to do.

The thing I truly love about Chicago is its real and raw character. From the wind blowing off Lake Michigan to the people with their Midwestern charm, there is just something special about this city. And with so many options for food, entertainment, and culture, you won’t have a moment to be bored during your weekend in Chicago.

Weekend Itinerary For Chicago

Image via Unplash by Pedro Lastra

Chicago ticks just about every box you could want in a city break. The food is second to none, the architecture is *chef’s kiss, and the Chicago culture is like no other. Our guide to the ultimate weekend in Chicago will include all of the above!

Whether you’re on an epic American holiday and looking to add a few days in Chi-Town to your itinerary or planning a weekend getaway with friends, this guide will help you make the most of your limited time in Chicago.

Day 1

Image via Flickr by Jasen Miller

Your first day in Chicago is all about getting to know the city and its iconic landmarks. The best way to do that is to make sure you’ve had your coffee and then head straight to Millennium Park. If you’re feeling like you want to hit the ground running, we recommend grabbing a pastry from Sweet Bean, it’s a Taiwanese Bakery with some unique little treats. You can get a coffee with a warm bun and be on your way.

Right in the middle of the city, surrounded by skyscrapers, you’ll find Millennium Park. This is definitely the place to start your Chicago itinerary. The park is home to so many of the city’s most iconic landmarks, including the famous Bean, also known as Cloud Gate. We’re sure you’ve seen the photos of the silver bean-shaped sculpture, but seeing it in person is truly a must. It’s even more impressive up close and you can get some really cool photos reflecting the city skyline on its shiny surface.

After snapping some pictures at the Bean, take a stroll through Millennium Park and marvel at the Crown Fountain, with its interactive video display of Chicago residents’ faces spouting water. You can also check out the Jay Pritzker Pavilion, an outdoor concert venue designed by renowned architect Frank Gehry.

Once you’ve explored the park, take a short walk over to the Art Institute of Chicago. This world-renowned museum has an impressive collection of art from all over the world, including famous pieces such as Van Gogh’s “Self-Portrait” and Monet’s “Water Lilies”.

This is one of the best art museums we’ve been to and it’s definitely worth a visit. We recommend giving yourself a couple of hours to fully explore the different collections in the museum. This is another option available on the Chicago CityPASS if you decide to go that route.

Okay, it’s the time we’ve all been waiting for… lunch! Eating in Chicago is an activity in itself. It’s not just food to keep you going through the day. It’s food that will change your life. Are we being dramatic? A bit! But you could spend your whole weekend just eating and we think Chicago would easily still become your favorite city.

For a classic Chicago experience, head to Giordano’s or Lou Malnati’s for some deep-dish pizza. This thick, cheesy, saucy creation is like no other pizza you’ve ever had and it’s a must-try when in the city. Now, some people scoff at the idea of deep-dish pizza, claiming it’s not really pizza at all. They say it’s lasagna in a crust. But we say, who cares? It’s delicious and that’s all that matters.

After lunch, take a walk down Michigan Avenue, also known as the Magnificent Mile. This famous street is lined with high-end shops and iconic buildings such as the Tribune Tower and the Wrigley Building. Even if you’re not in the mood for shopping, it’s worth taking a stroll down this street just to take in the grandeur and architecture of the buildings.

Once you’ve had enough of checking out the architecture from the ground it’s time to head to the water for a different perspective. One of our favorite activities in Chicago is taking an architecture boat tour on the Chicago River.

As you cruise along the water, you’ll have some epic views of the buildings and architectural masterpieces, all while learning about the fascinating stories behind them from expert guides. The tour usually lasts around 90 minutes so it’s also a nice way to relax and take a break from all the walking.

We know today is pretty jam-packed, but if you only have a weekend in Chicago, you want to make the most of it. And when you only get 2-3 sunsets in a city like Chicago, you want to make sure you have the perfect spot for each one.

So we are headed to Willis Tower, formerly known as the Sears Tower for sunset. The Sky Deck on the 103rd floor is one of the quintessential Chicago experiences.

From here, you’ll have a stunning 360-degree view of the Chicago skyline and if you’re feeling brave, you can step out onto The Ledge—a glass balcony that extends out from the building, giving you the feeling of standing in mid-air. You would think your brain would tell you not to step out onto the glass, but once you see everyone else doing it, it’s hard not to follow suit.

You’ll want to book your tickets in advance to make sure you get the time slot you want, this is super popular so we recommend booking as soon as you know you’ll be in the City. The time slots are all 30 minutes long so make sure you’re on time! This is also something you can add to your Chicago CityPASS.

Once the sun has set and the city lights start to twinkle, head back down to street level for dinner on the West Loop. This neighborhood has become a foodie paradise with renowned chefs setting up shop and creating some of the most innovative and delicious dishes in the city.

Girl and the Goat is our go-to spot. With celebrity chef Stephanie Izard in the kitchen, you’ll want to make sure to get a reservation well in advance. Enjoy small plates of creative and flavorful dishes like green garlic pierogis or wood-fired pig face (trust me, it’s delicious). Their cocktail menu also changes regularly, so it’s always fun to go and see what new concoction they’ve created!

After dinner, take a stroll around the West Loop neighborhood. Maybe pop in a cocktail bar. There is one on every corner, so just find one that fits your vibe. After a drink make your way back to your hotel for a much-needed rest.

Day 2

Image via Unsplash by Deborah L Carlson

After a good night’s rest, it’s time to explore more of this beautiful city. Today, we’ll be heading to the North Side to check out some of the city’s best museums, see Lake Michigan, and get a taste of the local culture.

Start your day by grabbing breakfast at Wildberry Pancakes and Cafe. There are a few different locations around Illinois, and to be honest, when you see it you might think it looks a little “chainy” and less like a cute boutique cafe. But don’t let that fool you – the food is amazing! Their menu is filled with delicious sweet and savory breakfast options.

Once you’re fueled up, head over to the Field Museum, also known as the Museum of Natural History. This museum is another attraction that can be included on your Chicago CityPASS. It has one of the best collections of artifacts and exhibits, including Sue the T-Rex skeleton and mummies from ancient civilizations. It’s absolutely HUGE, expect to spend a good 3 to 4 hours here. Even if you aren’t the biggest fan of science and natural history, this place is fascinating. It’s one of the largest natural history museums in the world.

Right around the corner from the Field Museum are the Shedd Aquarium and the Adler Planetarium. These two attractions are side by side and you’re more than welcome to spend your afternoons exploring both of them. But for time’s sake, we would recommend picking one and enjoying it fully.

The Adler Planetarium is a great option for those interested in space and astronomy. It has interactive exhibits and shows that will take you on a journey through our solar system, galaxy, and universe. Not to mention, the views of Lake Michigan from the planetarium are stunning.

If marine life is more your thing, then the Shedd Aquarium is the perfect choice. Home to over 32,000 animals from around the world, this aquarium offers a variety of exhibits including sharks, sea otters, penguins, and even beluga whales.

After a morning of being indoors, get some fresh air and explore the nearby Navy Pier. But before you make it all the way there, make a stop at Portillo’s for a classic Chicago hot dog. Now if you aren’t familiar with hot dogs in Chicago, they are not your average hot dog. They come loaded with a variety of toppings including pickles, tomatoes, onions, and mustard—almost like a burger. And they are so good!

Of course, they have traditional style glizzy’s (aka: hotdogs) as well if you prefer. But we think you gotta try the original at least once. Sit down, have some fries and a shake with your hot dog, and enjoy the Chicago vibes.

After you’ve gotten some food, continue to the Navy Pier. This is also an excellent activity for kids in Chicago. The pier is lined with boats of all shapes and sizes, restaurants, and even a few rides. It looks like a mini carnival with striped carousels and a giant Ferris wheel. From the Ferris wheel, you can get a beautiful view of the city and of the lake. Or just grab a drink at one of the rooftop bars.

As the sun starts to set, walk along the Chicago Riverwalk and take in the beautiful views of the city. The Riverwalk is a pedestrian pathway that follows along the Chicago River for 1.25 miles, with restaurants, bars, and cafes lining the way. It’s also full of free art installations, murals, and sculptures to admire. You can also take a guided tour with cocktails or rent a kayak to explore the river. This is definitely a touristy thing to do, but we are tourists after all!

For dinner, head to the Chicago Brewhouse on the river walk. It’s a casual pub with one heck of a draft menu. Most of the beers are German-style and made in-house. The food is also pretty tasty with a good variety of options. It’s right on the river, so you can sit outside, watch the boats go by, and fully enjoy a Chicago night.

Day 3

Image via Unsplash by Neal Kharawala

Today is a much slower pace, feel free to sleep in and relax before heading out for some more sightseeing. Plus, Sundays are for brunching in Chicago, so make your way to one of the many brunch spots in the city. We recommend heading towards Lincoln Park for some great options.

Our favorite is Summer House Santa Monica. Hear us out, we know we are in Chicago, and on the walk over you passed all the brownstones and the Chicago-style architecture, but trust us, this place is a hidden oasis on a warm day. Cali-inspired, the patio is a beautiful, airy space with string lights and greenery all around. And their brunch menu is delicious, try the avocado toast or the lemon ricotta pancakes.

After brunch, take a stroll through Lincoln Park Zoo (it’s free!) and enjoy some time outside before heading to your next stop at Wrigley Field!

Even if you’re not a baseball fan, Wrigley Field is an iconic part of Chicago’s history and worth seeing. Take a helicopter tour and fly over the stadium or, if you’re lucky, it will be baseball season and you can catch a game.

Get lost in the Wicker Park neighborhood after Wrigley Field. It’s full of small boutique shops and interesting street art. Join a guided tour to see the historic houses and cottages of the neighborhood. And if you’re feeling like a sweet treat, head to Stan’s Donuts. We seriously dream about Stan’s! They have this amazing lemon pistachio old-fashioned donut that is like heaven in a pastry. And during the fall months, their pumpkin spice donut is a must-try! Yeah, yeah we might sound like a fall-obsessed basic, but we know what we are talking about when it comes to pumpkin spice.

Exploring Chicago neighborhoods will give you an authentic look into the city’s culture and the day-to-day lives of its residents. The Pilsen neighborhood is one of our favorites and that’s why we’ve saved it for last. It’s best to make your way here before the sunsets so you have plenty of time to stroll through the colorful streets and admire the beautiful murals that cover most of the buildings.

This neighborhood has a strong Mexican-American influence, which you will quickly see in the food, art, and music. Make sure to try some delicious tacos from one of the local street vendors or stop by a bakery for some freshly made pan dulce (Mexican sweet bread). You can also check out the National Museum of Mexican Art to learn more about the history and culture of this vibrant community.

Personally, we think just soaking up the atmosphere here is the best way to experience Pilsen. Grab a beer from one of the local bars and sit outside to people watch or listen to live music. Our go-to spot is La Vaca margarita bar. It’s nothing special from the outside, but the sizzling fajitas are so good! You’ll get all the Mexican American vibes and the margaritas are top-notch.

Lastly, you can’t go to Chicago and not catch a show at one of the famous comedy clubs. The legendary Second City is where many famous comedians like Tina Fey, Bill Murray, and Steve Carell got their start. You can catch improv shows almost every night. The Laugh Factory is another popular spot that also features stand-up comedy shows.

If comedy isn’t your thing, Chicago also has one of the best Jazz scenes in the world. The Green Mill Cocktail Lounge is a historic jazz club that has been around since 1907 and still features live music almost every night. It’s most popular for being the hang-out spot of famous gangster Al Capone during the Prohibition era. It’s a great place to grab a drink, sit back, and enjoy some amazing talent on your last night in Chi-Town.

Map Of Chicago

Below is an interactive Google Map with every location previously mentioned for our weekend in Chicago pinned, which will help with your trip planning.

PRO TIP: Expand the map and create a copy in your logged-in Google account. With this copy, you’ll be able to access it in your Google Maps app under Saved. Scroll to the bottom and look for “Maps”.

More About Chicago

Image via Unsplash by Max Bender

Chicago is located in the northern part of Illinois along Lake Michigan in the Midwest region of the United States. The Chicago Metropolitan Area, also known as Chicagoland, includes the city of Chicago and its surrounding suburbs. With over 10 million residents, it is the third-most populous metropolitan area in the USA.

The city is often referred to as Chi-Town or of course, the windy city! Most people, us included, thought we would arrive and the wind would be an absolute nightmare. But, to our surprise (and relief), the nickname has more to do with Chicago’s politicians blowing hot air than the actual wind.

Chicago really took off in the 19th century and became a major industrial hub because of its location near the Mississippi River and the Great Lakes. They built an incredible transportation network with railways and highways, making it the go-to place for goods and people traveling all over the country. That’s how it became such a melting pot of cultures, which is super evident in its art, music, and food scene! It truly is what makes Chicago great.

Today, the city feels like a cool mix of history and modern flair. The skyline is breathtaking, especially with landmarks like the Willis Tower and John Hancock Center. Along with the gorgeous outdoors, the museums are top-notch. Chicago really knows how to combine charm with innovation, making it such a fun place to explore!

What To Pack For A Weekend In Chicago

Like all our other packing lists to come before, what to bring for this weekend itinerary largely depends on where you go. Like mentioned above, Chicago is the windy-city, so here’s what we recommend. And be sure to look into our Ultimate Cold Weather Packing List if you plan on traveling here in the winter months or 6 Minimalist Travel Packing Tips if trying to pack light!

• Light Jacket/Wind Breaker: While it’s not called the Windy City for excessive wind, it can still get pretty windy at times! Also available in women’s.
• Comfortable shoes: You’ll be fitting in a ton of walking during your weekend in Chicago so comfy shoes are an absolute must. This favorite brand of ours is also available in women’s sizing.
• Sunglasses: The shiny skyscrapers here are really good at reflecting the sun. The Maui Jim line are our favorite!
• Backpack: A backpack to carry all your things while exploring the city is highly recommended. Keeps your hands free for snapping pictures of the sights or to eat all the delicious street food!

Fun Filled Weekend In Chicago

If I’ve learned anything from my time in Chicago, it’s that a weekend in Chicago is always a good idea! From hot dogs and deep-dish pizza to the history and comedy clubs, Chicago is one of the best weekend getaways in the USA. It’s small enough to navigate easily but big enough that you will literally never be bored.

I hope this guide has given you a taste of what Chicago has to offer and inspires you to plan your own weekend adventure in the Windy City! Whether you’re checking out the cool architecture, exploring the city’s unique arts scene, or just relaxing in the city’s parks, Chicago has something for everyone.

Featured image via Flickr by MPBecker

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