While there's never a bad time to visit the Windy City, there are definitely some times that are better than others. If you're planning a trip to Chicago, you'll want to take the following factors into account in order to choose the best time for your vacation.
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Chicago experiences all four seasons, and each one has its own unique charm. However, if you're looking to enjoy outdoor activities during your trip, you'll want to visit during the warmer months. From May to September, temperatures hover in the mid-80s—perfect for a day spent strolling along the Magnificent Mile or enjoying a Cubs game at Wrigley Field. Just be sure to pack your jacket; Chicago is known for its windy days!
Events and Festivals
No matter what time of year you visit Chicago, there's sure to be a festival or event going on. Of course, some events are more popular than others. If you're looking to experience the city's vibrant nightlife scene, you'll want to plan your trip around one of Chicago's many music festivals, like Lollapalooza or Pitchfork Music Festival. Or, if you're a foodie, you might want to visit during Restaurant Week, when some of the city's best eateries offer special prix-fixe menus.
Hotel Rates and Airfare Prices
Of course, hotel rates and airfare prices are two of the biggest factors to consider when planning any trip. If you're looking to save a few dollars, you might want to avoid traveling during peak tourist season (basically summertime) or during popular holidays like Thanksgiving and Christmas.
Instead, try visiting during the shoulder season (April-May or September-October), when rates are lower, but the weather is still pleasant. Start by finding the perfect place to stay with Hotwire. Then pick up a rental car from Alamo Car Rental. Travelers can save money on their travels using these two great services that hook up consumers directly with what they need at competitive rates.
So when is the best time to visit Chicago? That really depends on what you're looking for in a trip. If you want nice weather and don't mind crowds, summertime is perfect for you. However, if saving money is your top priority, shoulder season might be a better bet. No matter when you go, though, we can guarantee that you'll have a good time—this city is amazing no matter what time of year!