Weekend Itinerary Chicago in Spring: 2-Day Itinerary

How to Spend a Weekend in Chicago in Spring: The Ultimate 2-Day Itinerary

Spring season is Chicago brings the magical blooms and kick-start the outdoor activities. Yes, As winter melts away and the Chicago city begins to bloom, spring in Chicago is best to experience.

Throughout the city outdoor patios start to reopen and you will be surprised to see locals enjoying outdoors the fullest.

If you’re planning a weekend trip to Chicago during spring then I would say that you’re in for a treat. Especially considering the weekend you have two days to explore.

In this post I will try to cover such a way that you can experience a little bit of everything such as architecture, food, nature, and culture. Yes, my comprehensive weekend getaway guide in Chicago during spring will help you enjoy the beautiful spring vibes.

Here’s how to spend an unforgettable spring weekend in Chicago.

Day 1: Weekend Chicago Itinerary in Spring

Time to explore downtown Chicago and Lakefront.

Morning: Millennium Park and Art Institute or Willis Tower

I recommend to start your Saturday in Millennium Park. You must see The Bean. Yes, Millennium Park is the home of the iconic Cloud Gate (aka “The Bean”).

This is a must-visit photo op especially in spring, the surrounding gardens begin to flower with tulips, daffodils, and blooming trees.

I suggest you to consider to visit Lurie Garden located just a few steps away from the Bean. In my opinion Lurie Garden is a peaceful oasis in the heart of the city.

Next, stroll over to the Art Institute of Chicago, one of the oldest and largest art museums in the U.S.

The Art Institute of Chicago features collections ranging from ancient artifacts to contemporary masterpieces (including Monet, Van Gogh, and Grant Wood’s “American Gothic”), it’s a perfect way to spend a spring morning indoors if the weather is a bit chilly.

Quick Tip: Purchase Go City Pass Explorer Pass or Chicago CityPASS to save on admission tickets to the Art Institute of Chicago.

If you are an architecture Buff then I highly recommend to Book a Chicago Architecture Center river cruise. This boat tour in Chicago is one of the top-rated tours in the city and even better on a sunny spring day.

If you are not a big fan of architecture and art collections, then you can choose Willis Tower, formerly known as Sears Tower. Willis Tower is also located few blocks walk away from the Millennium Park.

From top of the tower you will be able to see the great views of Chicago and neighboring states including our ocean like Lake Michigan.

I highly recommend to check weather before visiting Willis Tower. Because during spring season get lot of rain. If forecast is cloudy weather then DO NOT go to Willis Tower.

In cloudy rainy weather you will not have visibility of the city from the top. Avoid it period!

Quick Tip: Purchase Go City Pass Explorer Pass or Chicago CityPASS to save on admission tickets to Skydeck Chicago.

Lunch: Eat Local in the Loop

After soaking in some art or enjoying great city views from Skydeck Chicago, now it is time to grab lunch in The Loop.

You must be thinking why we call it The Loop? Yes, we call our downtown as “The Loop”. We Chicagoans call it “The Loop” because of the loop of elevated train tracks (the “L”) that circle the downtown area. This loop forms a rectangle around a core part of the city’s central business district, and the name stuck as a shorthand for the whole downtown area.

For classic Chicago eats I recommend to try out The Berghoff restaurant. It is a historic German restaurant that’s been serving the city since 1898.

If you are looking for a quick and diverse lunch then I recommend that head to Revival Food Hall where you’ll find everything from tacos to ramen under one chic roof.

For those who are more in the casual quick bites then I recommend to just walk down the Michigan Ave towards Chicago Riverwalk. You can find any quick bite places along the way such as Chipotle or Deep Dish Pizza Places such as Gino’s East Chicago Pizza or Lou Malnati’s Deep Dish Pizza.

You may also like my post on best deep dish pizzas in Chicago.

Afternoon: Lakefront Walk and Museum Campus

Spring is the perfect time for a Lakefront Trail walk or bike ride. If you are into bike then I recommend to rent a Divvy bike and cruise along Lake Michigan, soaking up skyline views and fresh lake breeze.

If you are not so much into biking then you can start walking towards Navy Pier in Lake Michigan direction on the walkway parallel to the Chicago Riverwalk. Personally I like the walk along Riverwalk towards Lake. It’s a quite long and scenic right next to the Chicago River.

Once you get there, you head south toward the Museum Campus. It is the home to the Shedd Aquarium, Field Museum, and Adler Planetarium. Also you can checkout Japanese Garden of Phoenix for cherry blossom blooms in Chicago.

Admission to these museums are included with both Chicago attraction passes at discounted price. You can either purchase Chicago Go City Pass or Chicago CityPASS. Trust me, you will save good amount of money on admission with one of these attraction passes.

If you have time then I recommend to visit one of the museums or simply relax outside and enjoy the panoramic view of the city from the planetarium steps.

Evening: Dinner and a Show

If you are bit tired and want to just relax for the night then I highly recommend to consider one of the dinner cruises from Navy Pier.

You are already on Museum Campus which is close from the Navy Pier. You can either enjoy a meal at Navy Pier or relax or you can just plan ahead and book a dinner cruise on Lake Michigan.

I highly recommend Odyssey dinner cruise. It is very popular among locals and visitors. So, I insist that you must book Odyssey dinner cruise in advance.

Click here to get the best deals on Odyssey dinner cruise on Viator.

For those who wants to keep exploring my lovely city Chicago, then I recommend that for dinner head to the West Loop. Yes it is one of the Chicago’s hot spots for foodie.

Quick Tip: For warmer days you can check out how to spend a weekend in the Chicago Loop.

In West Loop you’ll find everything from gourmet burgers at Au Cheval to upscale tapas at Avec.

If you’re craving Italian, Monteverde is a local favorite with handmade pastas that taste like they’re straight out of Rome.

To end the night with some relaxing time after dinner, you may consider to catch a show at Chicago Theatre or Second City.

Second City comedy is the legendary comedy club that launched the careers of Tina Fey, Steve Carell, and countless others.

Not sure but in my opinion, laughing the night away is a perfect way to wrap up your first day, so it is not a bad idea to include in your weekend itinerary in Chicago in spring.

Day 2: Weekend Chicago Itinerary in Spring

Let’s enjoy the neighborhood hopping and outdoor fun activities.

Morning: Breakfast and Lincoln Park

I always brag about us, Chicagoans, being foodie. Yes, No Chicago weekend is complete without breakfast or brunch.

You can get best breakfast anywhere in the city, but I recommend tourists to head to Lincoln Park and stop at Summer House Santa Monica for a bright, California-inspired brunch with lots of greenery and natural light.

If you’re in the mood for something cozy then Toast or The Original Pancake House are classic brunch spots.

Once you are fueled up with energy to explore the Chicago, then after brunch explore Lincoln Park Conservatory. It is a lush indoor garden filled with tropical plants and flowers. It’s free, warm, and smells like spring—even if the weather outside says otherwise.

Right next door is the Lincoln Park Zoo. Yes, one of the few free zoos in the country. It’s great for kids and adults alike. During spring season the animals are active and the landscape is blooming everywhere around the zoo.

Lunch: Picnic in the Park or Local Bites

If the weather is nice then to relax grab a bite to go from a nearby café and have a picnic in Lincoln Park or along the lakefront. You will have great time enjoying the views.

If weather is rainy or little chilly for you and you really prefer to stay indoors? Head to Old Town nearby for lunch at Twin Anchors, a classic Chicago rib joint that’s been around since 1932, or grab a sandwich from Potbelly’s, which originated in Chicago.

Afternoon: Wicker Park or Andersonville Vibes

Spend your afternoon exploring one of Chicago’s trendy neighborhoods. If you’re into indie shops, record stores, and cool cafés, check out Wicker Park/Bucktown.

I recommend to explore down Milwaukee Avenue where you can enjoy the vibes into vintage shops like Ragstock, grab a coffee at The Wormhole.

If you prefer a more laid-back and artsy vibe then head north to Andersonville. This Swedish-rooted neighborhood is full of charm, with shops like Women & Children First (a feminist bookstore), unique home decor boutiques, and cozy coffee spots.

Don’t forget to stop by George’s Ice Cream & Sweets if weather is warm enough for a scoop!

Evening: Rooftop Drinks or Riverwalk Dinner

In the evening I suggest to take advantage of spring’s longer daylight hours with rooftop drinks. The LondonHouse Rooftop, Cindy’s Rooftop, or The Robey in Wicker Park are few of the best rooftop bars with stunning views and seasonal cocktails.

I am sure you are going to enjoy the spring sunsets over the skyline are unforgettable.

Chicago Riverwalk is my one of the most favorite spot in downtown Chicago. I recommend to enjoy a dinner along the Chicago Riverwalk.

During winter season there is not much going on the Riverwalk but as soon as the weather starts warming up in spring season, this place comes to alive again.

Places like Tiny Tapp, City Winery at the Riverwalk, Chicago Brewhouse, or RPM Seafood are great options for dining with a view.

Majority of restaurants on the Riverwalk temporarily close down for the winter season. So, if you are traveling beginning of the spring season then I recommend to make sure with the restaurants before you plan your day in Chicago.

Spring Events For Weekend Itinerary in Chicago

So many festivals and events get started during spring in Chicago. Depending on your weekend, you might be able to catch. I recommend following to adjust your weekend itinerary in Chicago in Spring:

• Chicago Flower & Garden Show at Navy Pier
• Mayfest in Lincoln Park or Lakeview
• Chicago Humanities Festival
• St. Patrick’s Day Parade and the green-dyed river (if you’re visiting in March)
• Chicago Cubs or White Sox games – baseball season starts in April!

Click here to check discounted tickets for events in Chicago at StubHub!

What to Pack for Spring in Chicago

Chicago weather is very uncertain, especially during seasonal transition it truly gets unpredictable. So being a Chicagoan, I have sort listed few packing tips for Chicago in spring. Here’s my recommended quick packing list:

• A warm jacket or trench coat
• Comfortable walking shoes
• Umbrella or rain jacket (April showers are real!)
• Layers like sweaters or hoodies
• Sunglasses and sunscreen for those clear days

I highly recommend to use public transit or rideshare. Believe me avoid driving in city. Utilize public transit or rideshare to navigate easily around the city.

A spring weekend in Chicago is the perfect way to enjoy the spring season in Chicago. Like I always say that Chicago is the home of world-class museums to neighborhood charm, lakefront views to rooftop vibes, you’ll find a little something for everyone.

I must say that whether it’s your first visit or your tenth, Chicago in the spring never gets old. Also, my post on things to do in Chicago in spring season will be helpful if you are looking for an alternative for the activities in above 2-day Chicago itinerary for spring.

Planning your spring trip to Chicago? Apart from my weekend itinerary Chicago in Spring, also don’t forget to check out city passes: Chicago Go City Pass or Chicago CityPASS, tours, and hotel deals on Expedia.com and Booking.com to make the most of your visit.

So pack your bags, bring your camera, and get ready to fall in love with the Windy City in Spring season.