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If you’ve ever wanted to find out the best time to visit Chicago, what museums to visit, where to party at night, and what festivals you should keep an eye out for, this is the travel guide that has all the answers you need.
We’ll also cover the cheapest time to head to Chicago, how to steer away from the crowds, and when to avoid visiting. But first, let’s explore why visiting Chicago is worth your time to begin with.
Why You Should Visit Chicago in 2023
CHICAGO, IL – OCT 6: Cloud Gate and Chicago skyline on October 6, 2011 in Chicago, Illinois. Cloud Gate is the artwork of Anish Kapoor as the famous landmark of Chicago in Millennium Park./Songquan Deng/Shutterstock
Chicago has everything you can expect from an awesome international city, but let’s see what makes it truly stand out:
- The city has some world-class museums such as The Art Institute of Chicago, Museum of Science and Industry, Field Museum, Medieval Torture Museum, Chicago History Museum, American Writers Museum, Oriental Institute Museum, and Chicago Children’s Museum.
- The food scene in Chicago is much more creative than many anticipate at first. Our top foodie suggestions include deep-dish pizza, Chicago barbecue, Jibarito sandwich, The Rainbow Cone, pizza puffs, flaming saganaki, the Chicago-style hot dog, and an Italian beef sandwich.
- There are many tourist attractions worth exploring such as Cloud Gate, Skydeck Chicago, Buckingham Fountain, Wrigley Field, Navy Pier, Riverwalk, Shedd Aquarium, and 360 Chicago Observation Desk.
- Chicago is home to plenty of wonderful parks you can head to when the urban buzz feels like too much — our top picks are Millennium Park, Grant Park, The 606, Lincoln Park, Garfield Park, Jackson Park, and Northerly Island Park.
- Heading to some of the nearby lakes is another alternative for nature enthusiasts. While Lake Michigan is hands down the most popular one, others worth heading to include Rend Lake, Carlyle Lake, Chain O’Lakes Waterway, and Lake Shelbyville.
- The city’s beer scene is worth exploring, too. Beer lovers should take note of the following Chicago-based breweries: Metropolitan Brewing, Lagunitas Brewing Company Chicago, Goose Island Brewhouse, and Dovetail Brewery.
- Chicago is famous for its top-notch shopping districts. Be it a discount outlet, or high-end fashion, the city has you covered. Some of the best places you can go shopping during your stay there are Woodfield Mall, Andersonville, River North, State Street, Fashion Outlets of Chicago, and Water Tower Place.
Overall Best Time to Visit Chicago
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The overall best time to visit Chicago is in summer (June—August). It’s the busiest season for the city, when the weather is at its finest — temperatures are between 57°F and 84°F, so outdoor events are in full swing and beachgoing is at its peak.
The season is ideal for eating out or drinking on some of the city’s rooftops and patios, enjoying the free fireworks twice per week at Navy Pier, and exploring the city by embarking on a boat tour.
The summer festivals are a must, too — in June, there’s the Do Division Street Fest, promising live music, food vendors, and fun for the whole family each year; and the yearly Chicago Pride Parade.
July has the Square Roots Festival, a cool music and craft beer street fest, and Windy City Smokeout, a BBQ and country music festival that offers live country music, beer, and ribs. In August, the city hosts the world-famous Lollapalooza, a yearly four-day music festival, and Chicago in Tune, a citywide festival honoring Chicago’s versatile music scene.
The days can be quite hot and humid at times, but it’s nothing water recreation and festival going can’t make better. Also, as this is the most popular time of the year to visit Chicago, booking your stay in advance is mandatory.
Cheapest Time to Visit Chicago
Visiting Chicago in the fall (September—November) is the way to save some money. Airfare prices are more affordable, accommodation rates are reduced, and fall is generally considered to be the least expensive period to pay Chicago a visit.
The weather is still more or less pleasant — the temperatures vary between 32°F and 75°F. In early fall, you can even do almost every activity you’d do in summer in Chicago, just without the peak season tourists and through-the-roof prices.
The only thing to keep in mind is that certain attractions may have already reduced work hours, such as the Lincoln Park Zoo and the Navy Pier.
Popular fall events in September include Taste of Chicago; the world’s largest food festival held in Grant Park, Chicago Gourmet; Riot Fest, a yearly three-day punk rock music festival; Oktoberfest, where you can enjoy different beers and try authentic German food; Pitchfork Music Festival, an annual summer music festival organized in Union Park, and Hyde Park Jazz Festival, a yearly coming-together of jazz lovers.
In October the city hosts the popular Chicago International Film Festival; the Bank of America Chicago Marathon for travelers who wish to add more dynamics to their Chicago stay, and Chicago Beer Fest, offering a wide selection of breweries.
One of the most popular events in the entire year, The Magnificent Mile Lights Festival (November), is an annual event taking place the Saturday before Thanksgiving, where one million lights brighten Michigan Avenue on 200 trees.
Least Busy Time to Visit Chicago
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The least busy time to pay Chicago a visit is in spring (March—May). Spring is ideal for travelers who want to take advantage of the lack of crowds to explore Chicago in a laid-back way, as the temperatures are much milder than in winter — they typically range between 28°F and 70°F.
While it rains occasionally, this shouldn’t cause any major disruptions to your journey.
In terms of popular events around this time, mark your calendar for the following ones: St. Patrick’s Day Parade (March), when you can witness the Chicago River being dyed green; Chicago Restaurant Week (March-April), honoring the city’s culinary scene; Chicago Latino Film Festival (April), the longest running Latino film festival in the US; and Chicagoland Spring Marathon & Half Marathon (May), where you can either test your limits or cheer on other runners.
Worst Time to Visit Chicago
The worst time to visit Chicago is in winter (December—March). Chicago winters are infamous for being cold — expect below-freezing temperatures between 12°F and 36°F, and snow.
While certain winters are milder, the bottom line is that Chicago is much more pleasant in other periods of the year. Snowstorms aren’t that frequent, but make sure to always check the weather forecast and follow local advice if you’re there in winter.
Canceled flights or blocked roads aren’t unheard of and may impact your itinerary. Also, rivers are lakes may freeze, which translates into canceled cruises.
However, if visiting Chicago in winter is your only option, take the time to explore its museums, theaters, and comedy clubs.
Those ready to embrace Chicago’s winter conditions should keep an eye out for some popular outdoor events such as Christkindlmarket Chicago, a unique traditional market providing visitors with shopping fun, family-friendly events, and intercultural activities.
Other popular events around this time include Winter WonderFest (December-January), the city’s biggest indoor winter playground; the Garfield Park Conservatory Spring Flower Show (beginning in February), ideal for those looking to enjoy freshly blossomed flowers, and the Chicago Auto Show (February).
Things to Consider
Chicago, IL, USA – October 22nd 2021: View of an impressive fossil skeleton of a Titanosaur, one of the largest animals ever lived, at the Field Natural History Museum in Chicago, IL, USA/schusterbauer.com/Shutterstock
Trying to make the most out of your Chicago trip? Follow our travel tips to ensure you have a smooth stay:
- Chicago may not be the safest US city, but it’s far from unsafe for tourists, especially because most travelers navigate popular, crowded, and well-lit areas such as Loop and River North, and crime is more prevalent in its outlying regions.
- To save big on the city’s top attractions, consider buying a Chicago CityPASS, which grants you access to five attractions, or the Chicago C3 CityPASS, which covers three.
- Be on the lookout for museum discounts — these may include options such as student or senior discounts. Also, certain museums have free museum days.
- Get a CTA card to use public transportation — you can obtain it at any train station and most stores.
- Wear comfortable shoes, as you’ll do quite a bit of walking to navigate the city and see most attractions.
- Purchasing weed in Chicago is legal for anyone ages 21 and over. To buy weed products, you can check out some of the dispensary stores around the city. That said, make sure you buy them from licensed sellers and follow the laws. Namely, you shouldn’t smoke in public, within school premises, while driving, and so on.
- Chicago residents are said to be truly hospitable — if you need help with anything or simply wish to ask for directions, don’t hesitate to approach a local.
- Mondays in Chicago are generally very slow,and some attractions, such as the Art Institute of Chicago and Chicago History Museum, are closed. The same goes for smaller businesses. If you have some “big” plans for the Monday during your stay, make sure to double check the working hours of venues you wish to visit.
- Most Chicago restaurants don’t require a reservation, however, it’s highly recommended that you do make it beforehand.
- Get travel insurance.
Frequently Asked Questions
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Here are a few frequently asked questions to know about before going to Chicago:
Is Chicago expensive to visit?
For a three-day stay in Chicago, you’ll need $860 if you’re a solo traveler, $1460 if you’re going with a partner, and $1885 if you’re going as a family of four. Hotel prices in the city center vary between $200 and $500 (on average, $250 per night). You’ll need around $95 per day per person for eating out and transportation.
That said, note that the above-mentioned figures are merely estimates, as they come from other travelers’ data — your actual expenses will vary depending on your accommodation choices, the purchases you make during your stay, your departure city, and so on.
How many days do you need in Chicago?
We believe anything between three and five days should be enough to see most attractions, explore different parts of the city, and just enjoy the vibe of the city. If you want a more laid-back trip, opt for five days. If you have no problem sticking to a tight itinerary schedule, a three-day trip will do.
Do you need a car in Chicago?
No, you don’t need a car to navigate Chicago. You can get around just fine by relying on buses, trains, walking, or biking. That said, it’s a good idea if you want to take day trips from Chicago.
Which is better: Chicago or New York?
Both cities have a lot to offer in their own way — New York is much more vibrant and fast-paced, whereas Chicago operates at a much slower pace and is even family-friendly. Both cities offer an excellent gastronomy experience. That said, New York is considered safer than Chicago.
What European city is most like Chicago?
This may come as a surprise for many, but Berlin has been referred to as “the Chicago of Europe” by no other than Mark Twain, who wrote about this in an 1892 column for the Chicago Daily Tribune, referring to Berlin as the “German Chicago.” Note that this is a comparison mostly based on the two cities’ overall charms, and not so much on their physical appearance.
Book Your Trip to Chicago Today!
| 👍 Best Time to Visit | June to August |
| 💲 Cheapest Time to Visit | September to November |
| 🗓️ Least Busy Time to Visit | March to May |
| 👎 Worst Time to Visit | December to March |
So, with so much to see and do, what are you waiting for — book your trip today and experience for yourself all that Chicago has to offer. Happy travels!