What’s the best time to visit Chicago?

For travelers looking to experience the lively streets of Chicago, there is no single best time to visit. Visiting Chicago offers a special experience between either April and June or September and early November.

Not only do both of these periods offer great weather for sightseeing, but they also bring an abundance of events, festivals, and activities to the city. The clear skies, warm temperatures, and plenty of sunshine make these months ideal for exploring all Chicago has to offer.

From sampling deep-dish pizza in Little Italy to navigating your way through the Art Institute, it’s easy to see why so many choose this time as the best time to visit Chicago.

What is the weather like in Chicago?

The weather in Chicago can be quite unpredictable, especially during the spring and autumn months. In April and June, you can expect mild temperatures with highs in the mid-60s and lows in the 50s along with sporadic rain showers.

By September through early November, temperatures have usually cooled off to the mid-50s during the day and low 40s at night. However, frontal systems often bring colder air from the north, accompanied by temperature drops, gusty winds, and lots of clouds that can make it seem much cooler than it is.

Snowfall is possible but not common this time of year. Precipitation totals over these months tend to increase as well, making for wetter conditions as compared to summertime.

Where should I stay when visiting Chicago?

from incredible architecture to world-famous restaurants and shops. But where should you stay during your visit? Whether you’re looking for luxury or convenience, there are plenty of great options for lodging in the city. Let’s explore five of the best places to stay in Chicago.

Magnificent Mile Hotels

For visitors looking to stay in an area full of life, the Magnificent Mile is perfect.

This famous stretch of Michigan Avenue is home to many upscale hotels, restaurants, and attractions like the Navy Pier, Millennium Park, and the Museum of Contemporary Art.

Most Magnificent Mile hotels offer views of Lake Michigan or the Chicago skyline as well as easy access to public transportation. 

River North Hotels

Like Magnificent Mile hotels, River North also offers plenty of excellent options for lodging with a focus on convenience and comfort.

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This historic area features some of the best dining and shopping experiences that Chicago has to offer.

It is within walking distance from many popular attractions like The Bean at Millennium Park and Buckingham Fountain at Grant Park.

Wicker Park Hotels

If you’re looking for something a little different than the hustle and bustle of downtown, Wicker Park is a great option for lodging in Chicago.

This neighborhood features unique boutiques and artisanal shops as well as some of the best restaurants around town.

It’s just minutes from downtown by bus or train so you can easily explore all that Chicago has to offer while still having a quiet place to return at night with your choice of Wicker Park hotels. 

Hyde Park Hotels

Hyde Park is located just seven miles south of downtown on Lake Michigan’s shoreline and is home to two universities (the University of Chicago & University Of Illinois At Chicago).

It offers plenty of cultural activities such as tours at Robie House (Frank Lloyd Wright’s masterpiece), The Museum Of Science And Industry which houses a WWII submarine, plus excellent shops & eateries nearby.

With its convenient location on public transportation lines & proximity to downtown attractions Hyde park makes an ideal spot for visitors who want both exciting urban adventures & peaceful escape from city life.

Lincoln Park Hotels

Lincoln Park offers visitors classic urban living right next door to Lake Michigan’s beaches & parks.

Located just north of downtown this neighborhood provides easy access to both lakefront recreation & vibrant city life with its variety of shops & eateries plus its proximity to popular tourist destinations like Lincoln Zoo & Conservatory.

With its many hotel options ranging from budget-friendly motels to luxury high-rise towers, there’s something here for everyone seeking out short-term accommodations in Chicagoland.

What are the most popular attractions in Chicago?

With so much to explore, it can be difficult to decide where to begin your sightseeing adventure. To help narrow down your options, here are 10 of the most popular attractions in this vibrant Midwestern city.

The Magnificent Mile

The Magnificent Mile is an upscale stretch of Michigan Avenue located in the heart of the city. The area is home to some of Chicago’s most luxurious shops and restaurants as well as iconic attractions like the John Hancock Center and Tribune Tower. Whether you’re looking for a bite to eat or just want to take in some sights, this mile-long strip has something for everyone.

Millennium Park

Millennium Park is a sprawling 25-acre park located within Chicago’s downtown Loop district. It features a variety of attractions, including an outdoor amphitheater, public art pieces, and the world-famous Cloud Gate sculpture (better known as “the Bean”). As one of Chicago’s premier parks, Millennium Park sees millions of visitors each year.

Navy Pier

Navy Pier is a 3,000-foot-long pier that juts out into Lake Michigan from downtown Chicago. It’s packed with attractions such as amusement rides, theaters, gardens, and more! Navy Pier also hosts special events throughout the year such as fireworks shows on select summer nights and holiday celebrations during winter months.

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Art Institute of Chicago

The Art Institute of Chicago Located on South Michigan Avenue near Millennium Park, The Art Institute of Chicago houses one of the largest collections of impressionist art in North America. The museum also features modern and contemporary art exhibitions as well as the world-renowned Thorne Miniature Rooms exhibit – which showcases miniature replicas of European interiors from different eras.  

Wrigley Field

Wrigley Field is home to Major League Baseball’s beloved Chicago Cubs franchise. Built-in 1914, it’s one of baseball’s oldest venues and has been hosting games for over 100 years! A visit to Wrigley Field should be on your itinerary if you’re looking for some classic Americana vibes while in town.

Lincoln Park Zoo

If you’re searching for family fun activities while in town then look no further than Lincoln Park Zoo! Located just off Lake Shore Drive near North Avenue Beach, this zoo offers free admission every day and features exhibits ranging from African lions to Komodo dragons – making it an ideal spot for animal lovers young & old alike.


For those looking for spectacular views overlooking the Windy City skyline then make sure not to miss 360 CHICAGO observation deck located atop Willis Tower (formerly Sears Tower). This interactive experience boasts an enclosed glass balcony that allows visitors breathtaking views stretching up to four states away on clear days.

Grant Park

Last but certainly not least is Grant Park – a 319-acre urban oasis situated at the mouth of Lake Michigan where visitors can find everything from lush green fields & gardens to monuments & memorials dotted along its picturesque lakefront boardwalk path. A must-visit destination while in town.

What are the best restaurants in Chicago?

As locals, we know Chicago has some of the most delicious and unique cuisine around. From classic Italian to modern Mexican, there’s something for everyone. We’ve rounded up our 5 favorite restaurants that you have to try when you visit the city. Keep reading for all the details! 


This upscale restaurant has been a local favorite since it opened in 2005. Chef Grant Achatz and his team serve multi-course tasting menus with inventive flavors and combinations. Everything from the decor to the plating is designed to be visually stunning, so even if you don’t love every bite, it will be an unforgettable experience.

Au Cheval

For some of the best burgers in town (and possibly the country), head over to Au Cheval in West Loop. Their classic cheeseburger is topped with American cheese, pickles, diced onions, and dijonnaise sauce on a buttery brioche bun — a surefire hit! If you’re feeling adventurous, try their off-menu ‘double double’ with bacon jam or fried egg added on top for extra flavor.

Sable Kitchen & Bar

This chic spot offers elevated American cuisine with a twist — think dishes like grilled octopus and grilled lamb chops served alongside unexpected sides like edamame hummus and smoked potato salad. They also offer an extensive selection of craft cocktails that are perfect for sipping while dinner is being prepared in their open kitchen concept space.

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Frontera Grill & Topolobampo

Both Frontera Grill and its sister restaurant Topolobampo focus on authentic Mexican fare inspired by Chef Rick Bayless’ travels throughout Mexico City and Oaxaca over the years. From street tacos to slow-cooked pork tamales, this is some of the freshest Mexican food in Chicago that won’t let you down.


For classic Italian fare, look no further than Giordano’s famous stuffed deep dish pizza pie — arguably one of the best pizzas in town! They offer plenty of topping options as well as gluten-free crust so everyone can get exactly what they want out of their meal here — not to mention plenty of other delicious options like baked pastas and salads too! 

What are the best shopping areas in Chicago?

From beautiful boutiques on the Magnificent Mile to vintage stores and chic designer shops in Wicker Park, you’re sure to find something special during your time in the Windy City. Read on to discover five of the best shopping areas in Chicago.

The Magnificent Mile

The Magnificent Mile is a stretch of North Michigan Avenue between the Chicago River and Oak Street. This iconic street is packed with upscale retailers, including Neiman Marcus, Bloomingdales, Louis Vuitton and Saks Fifth Avenue. There are also plenty of well-known restaurants and bars here if you need a break from all that shopping.

Wicker Park/Bucktown

If you’re looking for one-of-a-kind items that are off the beaten path, head over to Wicker Park/Bucktown. This trendy area boasts an eclectic mix of boutiques, vintage shops, and art galleries. Here you’ll find everything from hipster clothing stores to unique home goods–all at prices that won’t break your budget.

Lincoln Park

Lincoln Park is one of the city’s most vibrant neighborhoods and it has become a popular destination for shoppers looking for high-end fashion labels as well as unique local stores. Here you can find designer brands such as Gucci, Prada, and Armani as well as smaller independent boutiques selling handmade jewelry and home decor items.

State Street

State Street is located downtown between Lake Street and Congress Parkway. This historic street has been a popular destination for shoppers since the late 1800s and it remains one of Chicago’s best spots for bargain hunting today. You’ll find department stores like Macy’s and Carson’s lining this bustling avenue along with several independent retailers offering discounts on clothes, shoes, accessories, gifts, electronics, books—you name it.

Randolph Street Market Festival

Randolph Street Market Festival takes place every third weekend of the month at Plumber’s Hall in West Loop neighborhood. It features over 150 vendors selling antiques & collectibles from around the world as well as locally made art & crafts. The market also has food trucks serving up delicious grub so you can refuel while browsing all those amazing finds.

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