The Dryftwell Guide to



Chicago's unique charm and history have been attracting tourists for decades. Surrounded by remarkable nature spots, a beautiful waterfront, lush green parks, skyrocketing scrapers, and fantastic architecture, Chicago is a chosen location for both nature-bound weekenders and city-sleekers. 

If you are eager to enjoy a blend of cultural experiences peppered with great happenings and snaps of the local lifestyle, then you are in for an amazing holiday.

In this guide to Chicago you'll learn about the city's different seasons, the top attractions to visit, popular neighbourhoods and transit details to help you move around town like-you-mean-it!

When to go


December to March is the winter season in Chicago, with 17°F to 32°F as the average temperatures. Visiting around this period means you'll get to join all the freezing winter-funs! Go ice skating and snowshoeing, join a winter garden tour and let the Chicago Restaurant Week fill your belly to the brim. During this major event at the end of Jan, you get to enjoy the food of different cuisines made by more than seventy top-rated chefs. What's more, the Chinese New Year comes around this time, so head to the Chicago Cultural Center with your peeps and relish in some ancient Asian traditions.  


April and May bring the blooms and spring scents to this beautiful city. The daytime is usually cool, but nights get windy. As Chicago in Spring is a top spot for visitors, you'll likely bump into crowds during your city exploits. But fear not! There's a lot of space for everyone here, so you'll get to explore at your ease. In this guide to Chicago, we recommend visiting the Field Museum and Shedd Aquarium for a family-friendly day outing. Also, make sure to devote some time to visit Navy Pier, Chicago's 3,300-foot-long pier and prime waterfront destination.


With temperatures averaging 80°F, summers in Chicago are not too hot. However, between June and August, you may need to shelter from thunderstorms, mad winds and pouring rainfall. This doesn't discourage visitors tho! Bustling with tourists, at this time of the year you'll get to see jam-packed parks and attractions, so come prepared. To enjoy your summer vacation in Chicago, hop on a boat cruise tour and sail around Lake Michigan and the Chicago River. You can also join many walking and drinking tours to check out popular trends as a local. One of everyone's fave outings is to take the beach tour where you can get your sandy-toes-fix at the prettiest Chicago beaches!


As the fall season brings all the magic of golden, red, and brown trees throughout the city, this is a spectacular time of the year to come to Chicago. With fewer tourists and moody fall vibes on-demand, fall is perfect for a couple's retreat or a fancy ladies weekend trip. To enjoy the city's true essence of fall, visit Chicago Botanical Garden, Lincoln Park, and Morton Arboretum. There are many other public parks that you can enjoy too, plus a slew of indoor activities such as museums, top restaurants, and a superb art scene.


Bucktown/Wicker Park

Bucktown is the artistic neighborhood of Chicago, popular because of its hip and trendy culture. So, if you want to experience the lifestyle of painters and musicians, this is the place to go. In the industrial area of Bucktown, you can dig some evening tunes with your family or loved ones. Because of its close distance to the downtown and affordable accommodation, it is prevalent among solo travelers and budget-travelers. You can see many sports arenas and fields in the region thanks to the people's great interest in the sports scene in this neighborhood. Also, there are many shopping places and restaurants that you can enjoy like Bento Box, Bucktown Gallery, and Le Bouchon.

Hyde Park

Hyde Park, also known as Chicago World's Fair, holds a traditional and amazing reputation because it is one of the first neighborhoods to be inhabited by early settlers. Visit this neighborhood and explore the beautiful and historic Museum of Science and History. Take a tour of the University of Chicago to learn about the educational system of the city, and head to Lake Michigan for blue waterfront views. If you are bringing the kiddies along, visit Chicago's serene parks full of walking and biking trails for you to enjoy.


If you consider yourself a big foodie and want to experience the authentic flavors of American and Mexican cuisine, we recommend you to take a tour of the Pilsen region in this guide to Chicago. Situated on the lower west side of the city, Pilsen contains tons of cool things to enjoy such as coffee shops, art galleries, live music, street food, etc. You can also attend the National Museum of Mexican Art if you love ancient arts and culture. All in all, this is a sweet spot in town thanks to its unique and fascinating vibe.




Driving in Chicago is extremely convenient because the city is well planned and has proper markings of roads and streets. Although you can expect traffic jams at times, especially in touristy seasons, you'll be fine! The average parking rate of a car is around $30, but it depends on the area you are parking. For getting around easily as a tourist, in this guide to Chicago we recommend you to use the iPark and Parkhero apps. If you do not want to use any map or just want to use a cab, you can easily book Uber or Lyft. 

Public Transit

Chicago stands among one of the top cities of the US because of its outstanding public transportation. You can use the Metra Rail Train to commute to some of the city's most popular areas and can use Shuttles and Ridesharing services. The most common way to travel to daily routes is by using the 'L' run by Chicago Transit Authority. The fare price is around $2, so it is considered the most economical way to travel. Apart from this, you can also use CTA's Bus service, but you will need to follow a strict timeline and check the schedule before booking. 


If you are a keen biker, we recommend you to travel using bikes in this guide to Chicago. You can use the locals' recommended bike-sharing service, i.e., Divvy, to travel all day around Chicago's many neighborhoods. Because the city offers a good bike lane infrastructure, you can use any bike type to enjoy. Also, it will be pretty easy for you to find the nearest bike station because they are spread throughout the city. People in Chicago love to walk! You'll see people moving around on foot at all times, so give it a chance and plan your itinerary accordingly!