Chicago in May is an ideal time to visit the city. The warm and pleasant temperatures allow you to easily explore the city’s many attractions and landmarks. Crowds and hotel rates are manageable, as it’s between spring break and summer break trips.
During this month, there may be rain which makes an excellent excuse to visit the many indoor attractions, such as the Navy Pier or one of the museums.
As a native who grew up in the area, I have detailed notes on the best times to visit Chicago, the weather, crowds, and clothing advice.
May is an especially excellent time, as it’s the first month you can take a dip in the water without getting too chilly.
It’s also really beautiful, as the parks and gardens are blooming and lush, providing a pretty environment for exploration.
See our unique Chicago May guide below for detailed notes on the weather, what to wear, and more for a smoother Chicago visit.
Tours/Activities | Our 3 Top Tips
In Chicago, the average high temperature in May is 70°F, about 11°F higher than the average in April. There are slightly fewer rainy days (eight) in May compared to April. Even with fewer rainy days in May, it’s best to bring an umbrella when visiting during this month.
Chicago in May weather begins with an average high of 62°F (17°C) at the beginning of the month. 71°F (22°C) is the average at the end of the month. Throughout May, the temperature slowly increases as the weather shifts toward summery June. The average rainfall is 3.4 inches.
In the mornings, you’ll find pleasant temperatures in the low 60s. If you’re a runner, the early mornings are the best time to be out as you can avoid crowds and the hotter mid-day temps. The temperatures are slightly higher in the evenings as they stay around the mid-60s.
💡 During the last week of May, sometimes we have days that feel summery as the temps can reach the 80s and even the low 90s.
However, these days are usually the rainiest, though the weather is generally still pleasant.
Average high temperatures in May:
- Early May: 62°F (17°C)
- Mid-May: 66°F(19°C)
- Late May: 71°F (22°C)
Typical temperature progression during a day in May:
- Morning (8 AM): 62°F
- Afternoon (3 PM): 68°F
- Evening (9 PM): 64°F
During the month, the average rainfall increases from 3.2″ to 3.7″. As mentioned, the rain typically increases as the temperature does in May. Most Chicagoans will carry an umbrella or wear water-resistant jackets on these days.
However, if the rain is light, I will often still walk around the city on foot. As a Chicago local, a little rain won’t deter me from getting outside after braving the chillier winter days!
What to Wear
In early May you typically wear lighter pants or shorts and t-shirts with light jackets in Chicago. As the month continues, most Chicagoans begin exclusively wearing shorts and t-shirts or short sleeve shirts.
The only time I don’t wear shorts is on rainy days when I instead wear lighter pants (cotton or similar material), a thin long-sleeved tee, a rain jacket, and rain boots.
Tip: As May offers warm yet wet weather, you’ll want to bring water-resistant shoes like galoshes or rain boots. Even with water-resistant boots, it’s always a good idea to bring extra socks in case your boots leak.
When visiting Chicago, it’s always best to carry an extra jacket or layers, especially if you’re an early riser or late-night explorer. The mornings and evenings can be windy, with some areas of the city (near the lake) which seem to be even gustier.
As the mornings are generally in the 60s in May, you can keep warm with a light jacket or sweatshirt. Ensure your jacket or sweatshirt has a hood to help protect your face from the wind.
Most of the time, I travel with a jacket in the mornings and evenings in May. However, one time I believed the weather would stay clear for the entire day. Unfortunately, it was raining within a few minutes after I left the house, so I had to change my plans to run back and grab an umbrella.
During the daytime, you’ll find the weather warms up slightly. At this point in the day, you won’t typically need a jacket (unless it’s raining).
If you plan to visit any museums during the day, I recommend bringing a coat as many museums keep the temperatures relatively low in the warmer months, and it’s easy to feel chilly inside.
However, outdoor activities should not require extra layers, especially if you’re doing something active such as running, playing frisbee or volleyball on the beach, etc.
What To Wear List
- Waterproof jacket (easiest way to stay dry in the rain)
- Waterproof boots/shoes (to help avoid soggy feet while in the city)
- Multiple pairs of socks
- Light sweaters/jackets (for cooler morning/evening temps)
- T-shirts/lighter blouses & shirts
- Dresses (for special occasions, get-togethers, dinners)
- Hat/gloves (only for those who run on the colder side)
- Swimsuit, beach towel, sunscreen (if you get a warmer, sunnier day)
While visiting Chicago in May, you’ll notice it’s getting busier due to the warmer temperatures. This month, the number of visitors and locals participating in activities is rising. You may have to wait in some lines, though the crowds are only moderate and overall manageable.
Outdoor and indoor activities are popular, depending on whether it’s raining or sunny. You will notice larger crowds at any events occurring during the month. As many people in Chicago stay inside for most of the winter, these events allow people to mingle with other locals.
💡 My favorite option for avoiding crowds is to arrive a few minutes before the museums open. This way, you’ll be first in line when the doors unlock. Arriving early has saved me many times from having to wait in line.
This choice came about after one particular day when I had to wait an hour to enter the Art Institute. Another trick is finding alternative entrances, like using the Monroe Street entrance for the Art Institute, as the lines are shorter than at the main entrance.
Memorial Day Weekend: Generally, the Thursday and Friday before Memorial Day, traffic is heavier in the city as locals travel to the suburbs to visit their families. Many travelers spend the long weekend in Chicago during this weekend due to the number of activities available, so expect the lines at popular attractions to be a little longer.
Otherwise, you won’t notice significantly more crowds in Chicago on Memorial Day and the weekend. You’ll also find that traffic on Monday is more hectic, as many Chicagoans are traveling back to the city before the work week begins.
Rates and Hotel Tips
Rates for Chicago hotels are moderate in May. The beginning of the month generally has slightly better pricing for hotels and flights. The price of accommodations and travel increase as demand increases, with more visitors toward the end of the month.
Weekends are pricier during May. If you want to get more affordable prices when booking accommodations, book at least 90 days in advance and travel during the week.
Our hotel tips for May with some of the best locations, so you can walk to the most intriguing places:
Fairmont Chicago Millennium Park
The staff is super friendly, our beds were very comfortable, everything was 100% clean and its location is perfect for a visit: It is only 1 block away from Millennium Park and Navy Pier. You can walk easily to so many hot spots during the mild May weather. It’s also quite close to Lake Michigan beach (20 minutes walk).
Trump International Hotel & Tower
This hotel offers spectacular views from every room! The view of Lake Michigan, the Chicago River, or the city skyline is iconic. It’s simply the best location when visiting in May. Very convenient to join a hop-on/off bus tour, walk along the river or to the Navy Pier, and walk to various restaurants and so many other area attractions.
The rooms are luxurious, and spacious, with everything you need.
Home2 Suites By Hilton | Budget Tip
This is our favorite budget hotel in Chicago! The location is excellent: It is located in Chicago’s River North district, a short walk from the Magnificent Mile’s (Mag Mile), shops, and restaurants. The Navy Pier, downtown, and the Chicago Loop are less than 15 minutes away.
Another thing we loved when we stayed there: You can prepare your own food in the room.
Things To Do
Tip: Make sure to grab the Chicago City Pass! It will save you a lot of money!
Many events occur in May, making it a great time to visit for everyone. Some notable events include the Spring Flower Show at the Garfield Conservatory and the Chicago Food Truck Festival. It’s also the first month that many farmers markets begin to open for the season.
May is one of my favorite months in Chicago; everything is opening back up, so there’s quite a lot to do! I love the farmers markets, as they have a large variety of items. Because of this, I’ll generally try to make it to the opening weekend with my reusable bags and cart!
Tip: Rent a divvy bike and ride around Lake Michigan. Depending on what part of the lakefront trail you’re on, you may catch glimpses of the iconic Navy Pier.
Below, you’ll find some exciting things to do and see while in Chicago this month, including some family-friendly activities for kids:
The Shedd Aquarium | Amazing for Kids
- Website: Shedd Aquarium
This is one of the most popular family attractions in Chicago. It houses more than 32,000 aquatic animals from all over the world, including dolphins, whales, sea otters, and sharks. It also features a 4-D Experience, interactive exhibits, and a Stingray Touch pool. Kids will love exploring the exhibits, interacting with the animals, and experiencing the 4-D movie theater.
Architecture River Cruise
- When: Year-round | Best in late spring and summer
- Where: Corner of Michigan (DuSable) Bridge
- Price: about $40 per person
May is the first month you can enjoy an Architecture River Cruise sans jacket! With the warm wind on your face and the views of Chicago, you’ll love this activity.
Chicago River architecture tours are a must-see for anyone visiting Chicago for the first time and May has the perfect weather for a memorable cruise. It’s a great way to get acquainted with the city while floating along on a boat.
Tickets and more information can be found here: Chicago River: 1.5-Hour Guided Architecture Tour. IMPORTANT: We highly recommend making a reservation in advance, as the cruises are very popular. However, you are free to try getting a ticket on short notice of course.
Navy Pier Centennial Wheel
- When: Year-round
- Where: 600 E. Grand Avenue, Chicago, Illinois 60611
- Price: $19.62 per person for standard entry, $30.52 per person for express entry
The Centennial Wheel is one of the most iconic activities in Chicago and a must-do in May. This 200-foot Ferris wheel offers spectacular panoramic views of the Chicago skyline, Lake Michigan, and Navy Pier.
As it can be busier on weekends during this month, please purchase the express tickets to jump to the front of the line. If you have children under the age of 2, they can ride for free.
Recommended tickets and more information can be found here: Chicago: Navy Pier Centennial Wheel Regular & Express Ticket.
Great for kids: Additionally, the Navy Pier itself is a great family destination with a variety of activities and attractions. It includes an interactive children’s museum, an IMAX theater, an amusement park, and a giant Ferris wheel. There are also many restaurants, shops, and live entertainment venues to explore in May. Kids will love the fun attractions, rides, and entertainment available at Navy Pier.
Art Institute Tour
- When: Year-round
- Where: 111 S Michigan Ave, Chicago, IL 60603
- Price: $115.54 per person
On the days during May when it’s too rainy to be outside, an Art Institute Tour is the best option. This tour will allow you to see the permanent and rotating exhibits in person.
If you’ve never experienced the Art Institute in Chicago, we highly recommend this tour in May. You’ll be able to recognize this famous building by the green lions that “guard” the exterior, which is also the meeting point for the tour.
Inside, you’ll be guided through sections of the museum that are filled with paintings, sculptures, and other mediums by the likes of Picasso and Rembrandt. Purchase skip-the-line tickets (highly recommended) and find additional details here: Art Institute Tour.
Walking by Lake Michigan
- When: Year-round
- Where: Lakefront trail off Fullerton Avenue
- Price: Free
May is the first time of the year when all the snow has melted in Chicago. There are no slippery or icy patches, so it’s the best time to go for a walk (or jog) next to Lake Michigan.
The lake is stunning to see, but nothing beats walking along the lake nearby Navy Pier on a sunny day in May. This route allows you to view the famous Ferris wheel with the skyline of Chicago in the background.
We love this route as it will take you alongside the beach. You can walk, jog, or bike ride on this path.
The Chicago Theatre Marquee Tour
- When: Year-round, great in May
- Where: 175 N State St, Chicago, IL 60601
- Price: $18 per person
This tour of the Chicago Theatre Marquee is a perfect activity to try on a rainy day in May. The tour lasts for 60 minutes and discusses the history of this building erected in 1921 as a movie theater.
Purchase tickets and find additional information here: The Chicago Theatre Marquee Tour.
The Magic Parlour
- When: Fridays + Saturdays year-round
- Where: 17 E Monroe Street, Chicago IL 60603
- Price: $79 per person
Take your family (12+ years old) to view a show at The Magic Parlour in Chicago during May. They offer fantastic magic shows! You’ll find a fancy yet intimate setting inside as only 50 people can view shows at a time.
There is a dress code for the shows, which is noted as cocktail attire. Expect to be called up on stage at any point during the show. The magician (Dennis Watkins) has been featured on larger TV channels like FOX, ABC, and WGN.
Find more information and purchase tickets here: The Magic Parlour Chicago.
Museum of Science and Industry
- When: Year-round | Great in May
- Where: 213 W Institute Pl, Chicago, IL 60610
- Price: $10 entry fee
The Museum of Science and Industry in Chicago is fun to explore science on one of those rainy days in May! With so many interactive exhibits and unforgettable experiences, exploring the museum might take more than one day.
Great for kids: The Museum of Science and Industry offers a fun and educational experience for kids. It features interactive exhibits, live science demonstrations, and a variety of programs and workshops. Kids will enjoy exploring the different galleries, learning about science and technology, and attending the many fun activities the museum has to offer.
What’s so cool about this museum? Stand inside a tornado, experience the world’s largest pinball machine, climb into a real-life WWII submarine, explore a coal mine, get lost in a mirror maze, and more intriguing things.
Field Museum of Natural History
- When: Year-round | Great in May
- Where: 1400 S Lake Shore Dr, Chicago, IL 60605
- Price: $26 ticket (subject to change)
Since the crowds are moderate, it’s an ideal time to see the Field Museum of Natural History without waiting in line for hours to enter. Like the Art Institute, this is a great rainy-day activity.
The museum holds over 35 world-renowned natural history exhibitions. Explore the subterranean life in the Underground Adventure exhibit. Experience the gemstones in the Hall of Gems and one of the largest collections of Chinese jade in North America in the Hall of Jades.
Great for kids: The Field Museum is a great place to take the kids to learn about natural history. It has a variety of exhibits, including dinosaur fossils, ancient artifacts, and cultural displays. Don’t forget to check out the Ice Age mammoth hunters and the temples of the Aztecs. Finally, visit the Dinosaur Hall Evolving Planet exhibit.
Your kids will love it!
360 Observation Deck
- When: Tours available throughout the year
- Where: 875 N. Michigan Avenue, Chicago, IL 60611
- Price: $30 per person
If you spend only a few days in Chicago in May, the 360 Observation Deck is a must-visit. Soaring 1,000 feet over Chicago’s legendary Michigan Avenue, 360 is one of Chicago’s most impressive attractions.
Tickets to skip the line (recommended) for a faster entry: 360 Observation Deck – Skip the Ticket Desk.
Outdoor events are abundant in Chicago during May. A few notable ones include – Mayfest, Bike The Drive, and the epic Memorial Day Parade. Mayfest runs for three days and offers what you would expect from a festival – live music, excellent food, and even a pet pageant. You’ll be able to find the Mayfest celebration under a tent.
‘Bike the Drive’ is an exciting event where Lake Shore Drive (one of the busiest streets in Chicago) is shut down. Bikers from all over will take to the street and ride a 30-mile course. If you’re a beginner, you can still join in on bicycle riding. It’s not necessary to finish the full course.
The Memorial Day Parade is created in honor of those who have served in the military. It is also meant to honor those who continue to serve. The day is filled with events related to honoring military personnel, including a wreath-laying.
Don’t forget to check out other Memorial Day weekend events like starting up the infamous Buckingham Fountain.