The Best Reasons to Visit Chicago in the Spring

Chicago is always a good idea. But there’s something a little extra special about visiting in spring. I’ve been to Chicago more times than I can count — every month of the year except July — and the energy the city has when it finally wakes up after winter is infectious. You can feel how excited everyone is.

Visit Chicago in the spring and you’ll see what I mean — flowers everywhere, rooftops opening and boats back on the river. It’s like the city has been in hibernation and is finally sticking its head out to see if it’s okay to come out. So pack your bags — and a coat just in case — we’re going to the Windy City.

Chicago Spring

Spring in Chicago is equal parts spectacular and unpredictable — which, honestly, is exactly what makes it so fun. You might get a perfect 65-degree afternoon. You might get a second, or third, winter that has everyone grabbing the coat still hanging by the door — because in Chicago, that coat never really goes away. Neither do the boots. Here’s what’s waiting when it thaws out in spring.

The Dyeing of the Chicago River

Meteorological spring in Chicago starts March 1st — but ask any Chicagoan and spring really starts the third Saturday of March when they dye the river green for St. Patrick’s Day. It’s a blast and no other city in the world that does anything quite like it.

The tradition goes back to 1962 when a local plumbers union used dye to trace illegal sewage dumping in the river and someone had the brilliant idea to lean into it. Now it’s a full city event with crowds lining up along the Riverwalk, in hotels on the river and even in boats and kayaks on the water.

The dyeing happens in the morning and within minutes the water turns a vivid, unreal shade of green. If you ever get the chance to go — do it.

Is it technically still winter? Yes. Does Chicago care? Absolutely not. The river dyeing is the city’s way of saying winter is over whether the calendar agrees or not — and once you’ve seen those green waters with the skyline behind them, you’ll understand why the whole city shows up for it every year.

The Tulips

Every fall, the city of Chicago plants tens of thousands of tulip bulbs across downtown and the neighborhoods for a spring show that stops people mid-sidewalk. What started as a Michigan Avenue tradition has turned into a city-wide event with colorful blooms popping up in parks, medians and gardens all over town.

The bulbs go in the ground in fall, get covered with sod to survive the winter and the snow melting chemicals, and then emerge at just the right time — and when the temperatures finally cooperate — to give the city hope after the long winter.

I love this tradition but what I really love is the backstory and how the city chooses the tulips. For example: one year they planted a Dutch variety that had been specially bred and named after Maggie Daley — the mayor’s wife, who was battling cancer at the time. Knowing she had carried tulips down the aisle at her wedding, the city planted that special variety as a show of support. That’s so Chicago — tough exterior but sweet on the inside.

If you want to see the tulips and catch them at peak color, aim for April through early May. You can’t miss them on Michigan Avenue, Grant Park and Millennium Park.

Lurie Gardens

Speaking of Millennium Park — yes, you have to see the Bean. You always have to see the Bean. I don’t care how many times I’ve been to Chicago, that shiny silver bean still makes my heart beat a little faster every single time.

While you’re there, walk behind it and find Lurie Gardens — my second favorite spot in Millennium Park and its best kept open secret. This two-and-a-half-acre garden is gorgeous in every season but spring is when it really shows off.

Tulips, peonies, native grasses and perennials all come to life at once — and peonies happen to be my favorite flower, so I am not exactly objective here. The whole thing feels like a secret garden that happens to be in the middle of one of the most visited parks in the country. It’s free, it’s stunning and almost everyone walks right past it to get to the Bean.

Bring a blanket. The lawns are perfect for a spring picnic and there are plenty of restaurants nearby if you’d rather not pack your own lunch.

The Views at 360 Chicago

I’ve always had a soft spot for the former John Hancock building. I went to the observation deck and the Signature Lounge bar on my very first trip to Chicago back in 2000. The view of the city and Lake Michigan from 96 floors up, or roughly 1,000 feet, is something I haven’t forgotten.

Sadly the Signature Lounge and Signature Room are both closed now but the building still delivers. The observation deck, 360 Chicago, took over the space and with it came a new bar — CloudBar — can be included with your ticket.

On a clear spring day you can see four states from up there. If you’re feeling brave the TILT ride leans you out over the edge at a 30-degree angle. Book your ticket for spring — the visibility before the summer haze rolls in off the lake is the best.

Architectural Tours on the Chicago River

Chicago has one of the most remarkable skylines in the world and the best way to see it is from the water. Spring is the ideal time for an architecture boat tour — the crowds are smaller than summer, the light is beautiful and the river has that just woke-up like the rest of the city.

The tour takes you along the Chicago River through the heart of the city with a knowledgeable guide explaining the history and design of the buildings passing overhead. You’ll see the city from a perspective you simply can’t get from the street.

There are several tour operators but Wendella Boats is my recommendation — their tour guides are excellent, the boats have both indoor seating and an open air upper deck plus they even serve mimosas on the morning tours. The tour runs about an hour and a half and is worth every minute.

The Chicago Riverwalk

Walking the Riverwalk is one of the best things to do in Chicago on a spring day — restaurants and bars are opening their outdoor spaces, kayaks are back on the water and you never know what you might discover along the way. This 1.25 mile pedestrian friendly path runs along the south bank through the Loop between Lake Michigan and Lake Street.

When you don’t know what else to do or don’t feel like doing anything else, grab a coffee, walk the Riverwalk and find a spot to sit by the water for a while. It’s free, it’s mostly flat but for some stairs in a few places, and it’s one of those things that’s easy but still gives you the I did something great in Chicago today feeling.

Rooftop Bars

Who doesn’t enjoy sitting outside sipping a libation or two on a nice spring evening? After the long winter, Chicagoans are eager to get outside some fresh air — even if you do need a light jacket. Spring in Chicago means the reopening of restaurant and bar rooftops. These three should be on your list.

Cindy’s at the Chicago Athletic Association Hotel on Michigan Avenue has panoramic views of Millennium Park and Lake Michigan from the 13th floor. The cocktail menu is creative and the setting is one of a kind with a direct view of The Bean — this is the one I’d go to for a special occasion or a long spring brunch.

LondonHouse Rooftop on the 21st floor of the LondonHouse Hotel has what I think are the best views of the Chicago River and the skyline. Classic cocktails, small plates, sometimes live music. Go after dinner and stay as long as they’ll let you.

Cubs Opening Day at Wrigley Field

There are few experiences more quintessentially Chicago than Opening Day at Wrigley Field. The ivy isn’t back on the walls yet — that comes later in the season — but the vibe more than makes up for it. The entire Wrigleyville neighborhood comes alive, the bars across from the stadium fill up and the city is ready for baseball.

You don’t have to be a Cubs fan to enjoy it. Wrigley Field is one of the great ballparks in America and Opening Day has a feeling that regular season games just don’t replicate. If you can get tickets, go. If you can’t, just the neighborhood on a game day is fun. Opening Day 2026 is March 26th.

Chicago Spring Festivals and More

One of the things that makes Chicago a great city is that there is always something going on — and spring is when the event calendar starts filling back up.

The Chicago Latino Film Festival and the Chicago Kids and Kites Festival are two popular spring events to know about. And the Memorial Day parade wraps up the season in classic Chicago fashion.

Lincoln Park Zoo gets in on the action too — the Spring Egg-Stravaganza brings an Easter egg hunt, carousel rides and zoo experts to the grounds in April, and the Run for the Zoo 5K and 10K takes over the zoo’s scenic paths in early June.

This is just a small sampling because Chicago literally has a festival for everything. Check the city’s official events calendar before you go — you’ll almost certainly find something happening that weekend that isn’t on anyone’s list yet. And coming soon: a new presidential library!

Chicago Weather in Spring

Chicago weather in spring will do whatever it wants and there’s nothing you can do about it. At times it defies the weather forecast. It might run the full range from winter to summer in the same week if not the same day.

April is the most unpredictable month. May is generally more reliable but “generally” is doing a lot of work in that sentence. And I’ve even seen big swings in June.

One of the most extreme was a Friday in an April weekend when it was so cold and windy with even a few flurries, it had me questioning why I was there waiting in line outside for an event. Then by Sunday it was 80 degrees and we were eating outside on a patio. It turned out so pretty we extended our stay. That is Chicago.

What to pack for Chicago in spring:

• Layers are non-negotiable — a light jacket isn’t enough, bring something a bit warmer too
• Boots or at least closed-toe shoes for the inevitable cold snap
• A packable rain jacket takes up almost no space and you will probably use it
• Comfortable walking shoes — Chicago is a walking city and spring is when you want to be outside
• Sunscreen — when the sun does come out it reflects off the lake and the buildings

The upside of unpredictable weather is that you appreciate the good days in a way you simply don’t in a place where it’s always nice. A warm sunny day in Chicago in April feels like a gift.

FAQ

Is Chicago Safe to Visit?

Chicago has a few neighborhoods with higher crime rates like most large cities do but the areas most visitors spend time in — the Loop, River North, Lincoln Park, Millennium Park and the Riverwalk — are safe, busy and well-patrolled. Use the same common sense you’d use in any major city: stay aware of your surroundings, watch your bags and wallet and stick to well-lit areas at night. Most visitors have no issues at all.

Is Chicago Worth Visiting in April?

Absolutely — just know that you need to pack for anything. April is when the tulips are at peak color, the rooftop bars are starting to open and the city has that electric just-woke-up energy that makes spring in Chicago so special. The weather is unpredictable but that’s part of the experience. Come prepared and you’ll love it.

Do I Need a Car in Chicago?

No — it’s kind of a hassle actually. Parking is hard to find and paid lots are expensive. Chicago has good public transit with the CTA El train and buses covering most of the areas visitors want to be. Rideshares are everywhere with little waiting and the city is very walkable in spring. Save the rental car for day trips outside the city.

Where to Stay in Chicago

The Loop and River North are my go-to areas and where I send most clients. Both put you within walking distance of Millennium Park, the Chicago River, the architecture boat tours, Michigan Avenue and most of the rooftop bars in this article. You’ll spend less time in rideshares and more time actually enjoying the city.

The Silversmith Hotel in the Loop is one I keep coming back to — it’s a historic property with great bones, well-located and a solid value for what you get in that neighborhood. It’s the kind of place that feels like Chicago rather than a generic business hotel.

River North has a wide range of options from boutique hotels to larger properties and is particularly good if you want to be close to the restaurant and bar scene. Hilton Garden Inn, River Hotel and Kinzie Hotel in River North are all conveniently located to the river and Michigan Ave.

And then there’s The Drake. It’s been on my wishlist for so long — every time I’m driving down Lake Shore Drive and make that curve where Michigan Avenue opens up and the Drake comes into view, I get chills. That view is one of my favorites in Chicago. One of these days I’m staying there and I’ll report back.

A few things to be aware of: spring rates are generally lower than summer but can spike around major events like Opening Day, St. Patrick’s Day weekend and Memorial Day. Book ahead if your dates overlap with any of those times.

Planning to Visit Chicago in the Spring

Here’s what I’d tell any friend asking: yes, Chicago in spring is worth it. The tulips are out, the rooftops are open, the river is busy and the Bean is always there. Come prepared for anything and you’ll leave wanting to come back.

Pack layers. Bring comfortable shoes. And leave some room in the itinerary to just wander around.

Ready to plan your Chicago trip? I can help with hotels, itineraries and making sure you don’t miss the good stuff. Fill out this form or shoot me an email — I love talking about Chicago.

See you at the bar!