The best time to visit Chicago depends on your motivations for making the trip. Every season has its special perks and challenges. For starters, it might seem easy to write off winter travel to Chicago. This is a city that names its snowstorms.
Anyone remember Snowmageddon?
Here’s the thing. If you pack right and embrace a little extra flexibility, Chicago winters can be magical.
Let’s take a look at the real best times to visit Chicago and all of the fun you can have in the city no matter when you choose to go.
When Is the Absolute Best Time to Visit Chicago?
If we’re being honest, the best time to visit Chicago is in the shoulder seasons. September and October are ideal for lower prices on flights and accommodations and decent weather. May is great too. The days are warm and usually dry enough to enjoy them. Just avoid spring break if you’re traveling on a budget.
Want Cheap Flights and Hotels?
It doesn't get more budget-friendly than Chicago in the winter. Flights are cheap and accommodation is even cheaper. Hotels are not operating at full capacity by the time January comes around because of the city’s challenging winters, so it’s a great time to snag an offer.
If you don’t want to deal with winter travel but love good deals, just avoid peak summer travel. You can still pay less for a trip to Chicago as long as it’s not from Memorial Day weekend through Labor Day.
Want Good Weather?
The best time to visit Chicago if you’re looking for good weather is early summertime. If you love those warm temperatures but have sticker shock over summer travel prices, September into mid-October usually stays quite warm. Of course, maybe you consider “good” weather to be a blanket of beautiful snow! If that’s the case, aim for January and February.
Chicago in the Spring
Most Chicagoans will tell you that spring can be hit or miss in Chicago. It’s not unheard of to see snow flurries in March, but it’s also when locals start to wake up from the winter blues.
We know you’re looking for good deals, so skip spring break and Easter if you can. If you visit around St. Patrick’s Day (March 17), you may get the chance to see the city dye the Chicago River green and, perhaps surprisingly, prices usually stay pretty budget friendly during this unique event.
Here are a few more highlights for Chicago in spring:
- See the Garfield Park Conservatory Spring Flower Show. The show typically starts by the end of February and runs well into May.
- Stroll along Michigan Avenue. By about mid-April, the tulips planted along the medians in Chicago’s downtown start blooming, making quite the colorful sight.
- Visit Lincoln Park Conservatory. Spring days are the perfect time to visit some of Chicago’s scenic spots. Don’t miss the Alfred Caldwell Lily Pool.
Chicago in the Summer
Summertime is peak season in Chicago for a reason. The city comes alive with events to signal the official end of winter. (We know we just talked about spring in Chicago, but locals know spring cold snaps are a real thing.)
If you’re traveling to Chicago in the summer, expect crowds, steamy weather, high prices on airfare and accommodations, and a packed calendar. Here are the top things to do in Chicago in the summer:
- Attend a summer festival. You need to do some planning if you want to go to Lollapalooza, but the Chicago Blues Festival and Windy City Smokeout are just as good and easier to get tickets for.
- Go to the beach. Pack a swimsuit because the lakefront is where it’s at for Chicago summers. North Avenue Beach is most popular. Foster Beach is more mellow.
- Kayak along the Chicago River. You don’t need any of your own gear. Book a tour with one of many outfitters like Kayak Chicago who take small groups out onto the water.
Chicago in the Autumn
Fall in Chicago means leaf peeping in the city’s urban green spaces. Temperatures typically don’t drop to uncomfortable levels until after Halloween, so you’re in for more treats than tricks if you visit in autumn.
If you want to save money on your trip, avoid traveling to Chicago over Thanksgiving. Thanksgiving is generally an expensive time to fly anywhere domestically — to be honest, you’re better off traveling abroad if you’re looking for cheap flights at that time! — and Chicago is no exception.
Let’s take a look at Chicago’s best fall activities:
- Get spooky at the Night of 1,000 Jack-o'-Lanterns. Travel to suburban Glencoe for this sellout event at the Chicago Botanic Garden.
- Go leaf peeping. Wander any of the city’s neighborhoods and you’re sure to find those blazing colors. Lincoln Park or Humboldt Park are a great starting point.
- Snack on sweets at Lincoln Square Ravenswood Apple Fest. This annual October event is all about welcoming autumn with the best fall flavors.
Chicago in the Winter
You’ll probably need to bring a bigger bag to fit all of the warm clothes you’ll need for a winter trip to Chicago, but there are good deals to be had on the other side of that added effort.
What we’re saying is, good things come to those who pack warm.
Just keep in mind that there’s a learning curve for winter travel in the Midwest. Plan for extra travel time and make sure you’re equipped to drive through inclement weather if you’re renting a car.
If you’re ready for cold temps and hot deals, here are a few things you shouldn’t miss during a Chicago winter:
- Ice skate on the Skating Ribbon at Maggie Daley Park. The ribbon is twice the length of most skating rink laps. Hot chocolate awaits when you’re done.
- Sip on German Glühwein at the Christkindlmarket. That’s mulled wine, by the way. The annual German holiday market also sells sweet treats and trinkets.
- See the frozen lake. You’re likely already all bundled up. The Lakefront Trail is a great place to start for the best wintry scenes.
Save Money on Chicago Travel
There really isn’t a bad time to visit Chicago. For some travelers, it comes down to how they’d like to spend their time in the city. For others, it’s about making sure their Chicago holiday is budget-friendly. Since it’s impossible to know what kind of weather you’ll really have, book when you’re able to find cheap airfare and hotel deals and pack accordingly. That’ll make your trip just as rewarding. SuperTravel has thousands of accommodation options throughout the Chicago area, book now to save up to 50%!
