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Chicago is spectacular, and many travelers have fallen in love with it, after only a few days of sticking around. Being America's third-largest city, there is a lot to experience, ranging from incredible shopping opportunities to a fantastic dining scene to several entertainment options. The Windy City boasts top-tier attractions, breathtaking city scenery, and waterfront views that every vacationer would definitely marvel at.
Lying along Lake Michigan, Chicago is one of the best places in the world to experience 20th-century art and architecture at its most impressive. Wondering what to do in the Windy City? Here is an ultimate guide to Chicago.
When To Visit Chicago
April through June and September to early November are the best times to explore the Windy City. While other vacationers may prefer other months of the year, these are the most appealing times, based on good weather, crowds, and incredible sights to see.
Visitors looking for good weather should definitely be in spring and autumn. Summer is the peak tourist season, characterized by hiked prices in accommodation, restaurants, flights, and even sightseeing.
For cheap prices, vacationers planning a visit to the Windy City on a budget should opt for the winter months. January and February are the cheapest months in winter, as the vibrant celebrations and events are over, making them the best time for budget vacationers.
One can get as much as 50% or more discounts in the finest establishments in the city.
Between June and September is the perfect time to explore Chicago with kids, as there are several family-friendly activities to enjoy.
Since the attractions are extremely crowded and expensive to access, August is an excellent time to plan a visit to the Windy City with kids, as things get more affordable, as the crowds become thinner.
Weather also becomes less extreme than in July.
Food buffs should target Chicago during festivals, such as the Chicago Pizza Party in February and the Chicago Hot Dog Fest in August! One can also visit the city between mid-March and early April for Chicago Restaurant Week.
The biggest food festivals take place during the peak season, the Taste of Chicago in July and the Chicago Gourmet festival in September.
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For the most impressive outdoor opportunities, vacationers should try and visit from September through November, which is when the surrounding changes into gorgeous browns, reds, and yellows, creating awesome scenery.
Summer is also a good time for outdoorsy visitors, thanks to the 26 miles of magnificent Chicago beaches. The hot weather and warm waters make it an ideal time to go swimming, snorkeling, or scuba diving to explore the underwater world.
- Best time for good weather: Spring and autumn
- Best time for cheaper deals: Winter months, especially January and February
- Best time for families: August
- Best time for foodies: February, August, Mid-March-Early April, July, and September
What To Know Before Visiting Chicago
Public Transport Is The Most Affordable And Reliable Way Of Getting Around The Windy City
Regardless of where vacationers fly into, Midway or O’Hare, the Chicago Transit Authority’s L train can get to any destination, from the airport to downtown and beyond.
Vacationers should always look at the CTA map because most of the destinations in their bucket lists have a CTA stop. CTA operates eight L lines and 140 bus routes, so visitors can always reach their destinations.
Ensure You Get A Ventra Card To Save Money On Transport
With Ventra Cards, getting around Chicago is easy-peasy. Travelers can find these cards in any L station, including airports. The cards allow one to save about $0.75 per ride.
Travelers have the option of loading these cards with money or buying one-day, three-day, or seven-day passes.
Buy Tickets For Exploring Museums And Theaters In Advance
Many museums and theaters in Chicago require vacationers to buy tickets online in advance. A week ahead is great, and one can buy them through the museums’ or theaters’ websites.
Make Restaurants Reservations
There are plenty of Michelin-starred restaurants in Chicago that travelers would love to explore. For the best experiences, make reservations, especially for weekend dining.
Some restaurants may require a week or two prior bookings, while hot spots may need one to make reservations a couple of months out.
How You Can Get Around In Windy City
Public transportation is, of course, the best way to get around Chicago, not just because it is the most affordable, but it is also simple to use and navigate through.
The Chicago Transit Authority (CTA) operates the city's transportation system and has routes covering almost all the attractions. Travelers can choose the L Train, which is the best option, the bus, or Metra Rail to reach various destinations.
Taxis, water taxis, and cars are other options to consider. Taxis are perfect for travelers looking to get to destinations beyond downtown Chicago. A cheaper alternative is ridesharing via Uber or Lyft.
Vacationers can also use water taxis along the Chicago River and Lake Michigan to get to some of the most popular areas in the city, including the Museum Campus and Chinatown. Vacationers planning to get around Windy City in cars should prepare for hefty parking costs, and heavy traffics, especially during peak hours.
Where To Stay In Chicago
Travelers have several accommodation options in Windy City no matter their budgets and interests. Try one of these fabulous hotels:
The Peninsula Chicago (Luxury Option)
With its central location in Chicago, The Peninsula Chicago is perfect for vacationers looking to stay a few steps away from the city’s iconic attractions.
- Address: 108 East Superior Street, Chicago, IL 60611
- Amenities: Indoor pool, spa & wellness center, fitness center, restaurant, bar/lounge, room service, free Wi-Fi, coffee machine, coffee shop, and Wi-Fi available in all areas.
Virgin Hotels Chicago (Mid-Range)
Virgin Hotels Chicago is also located in the heart of Windy City, only a short distance away from Chicago Riverwalk and Chicago Theater.
- Address: 203 North Wabash Avenue, Chicago, IL 60601
- Amenities: Fitness center, restaurant, bar/lounge, room service, free Wi-Fi, tea/coffee maker, coffee machine, coffee shop, valet parking, and business center.
River Hotel (Budget Hotel)
River Hotel is located only a few steps away from the Chicago Riverwalk and Michigan Avenue and boasts world-unique amenities and facilities for its guests.
- Address: 75 East Wacker Drive, Chicago, IL 60601
- Amenities: Fitness center, restaurant, bar/lounge, room service, free Wi-Fi, coffee machine, valet parking, business center, and Wi-Fi available in all areas.
Where Can You Eat In Chicago
Chicago’s food scene is one of the most incredible, and exploring the best places can be challenging, especially for first-timers with an appetite for everything. Here are the top places to check:
- Galit Restaurant: Located in Lincoln Park, Galit is a newer development of the area and an incredibly fun place to grab some eats, especially for dinner. the food eatery specializes in Middle Eastern dishes, and vacationers can enjoy a lot, including roasted carrots, spicy shakshuka, and creamy hummus.
- J.P. Graziano Grocery & Sub Shop: If looking for a place to break for lunch while exploring the city’s beautiful sites, this is the perfect spot. Opened in 1937, this family-run restaurant offers some of the tastiest Italian sandwiches in the city.
- Do-Rite Donuts & Chicken: For breakfast, head to this amazing restaurant. Have a taste of their Applewood smoked bacon, Vera Cruz, and chicken sausage & egg sandwich.
Fun Things You Can Do In Chicago
Explore The Art Institute Of Chicago
Travelers can enjoy exploring hundreds of thousands of beautiful art pieces at the Art Institute of Chicago, a world-class museum worth visiting. These artworks are from different periods in history and include textiles, photography, painting, prints, architectural drawings, and sculpture, among others.
The museum is home to art and architectural works from some of the best artists and architects the world has ever known, including George Seurat. Art lovers can't afford to include one of the best museums in Illinois in their bucket lists.
- Tour: Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket
- Duration: 2 hours 30 minutes
- Cost: From $115.54 USD per adult
Stroll Through The Millennium Park
Located in downtown Chicago, Millennium Park is a portion of the Grant Par and is the largest public space in the area. Established in 2004, the park is one of the best attractions in Windy City to explore for free.
Millennium Park is situated on the east side of the district, surrounded by Michigan Avenue on the west part, Columbus Drive on the east, Randolph Street on the north, and Monroe Street on the South.
The main attraction at the park is the Cloud Gate, an incredibly stunning 110-ton sculpture that can be seen reflecting the surroundings, including the sky, people walking around, and the buildings.
- Tour: Chicago Millennium Park Self-Guided Walking Tour
- Duration: 20 to 30 minutes
- Cost: From $8 USD per adult
Walk Around The Navy Pier
Constructed in 1914, Chicago’s Navy Pier has gone through a lot of changes ever since it was established as the largest pier in the world. The pier measures 292 ft wide and 3,000 ft long, built for shipping goods and entertainment.
Today, it’s an amazing cultural hub where vacationers can explore various things, including over 50 acres of beautiful gardens, a wonderful dining scene, arts, colorful shops, parks, and concert venues. This is one of the places in Windy City that vacationers can’t afford to miss.
- Tour: Experience Wed & Sat Chicago Fireworks Aboard Tall Ship Windy from Navy Pier
- Duration: 1 hour 30 minutes
- Cost: From $79 USD per adult
Take Kids To The Adler Planetarium
Chicago's Adler Planetarium is one of the top places that visitors can visit with kids, but vacationers of all ages are definitely going to relish being there. Constructed in 1930, along Lake Michigan's spectacular shore, the Adler is the first planetarium in the Western Hemisphere.
There is a lot to experience, especially in the two dome theaters located at the planetarium, including numerous shows and exciting exhibits that cover the exploration of space, the history of astrology, and more fun and educating topics to discover.
Chicago is an amazing destination to explore, as it has everything for every traveler. From museums with fascinating exhibits to top-tired restaurants to top-rated hotels for accommodation, visiting Windy City is definitely worth it.
FAQ
Q: What is the best time to visit Chicago?
April through June and September to early November are the best times to explore the Windy City. While other vacationers may prefer other months of the year, these are the most appealing times, based on good weather, crowds, and incredible sights to see.
Q: What to know about traveling to Chicago?
There are certain things vacationers should know before they visit Windy City. They include:
- Public transport is the most affordable and reliable way of getting around the Windy City
- Get a Ventra Card to save money on transport
- Buy tickets for exploring museums and theaters in advance
- Make restaurant reservations
Q: How do you get around Chicago safely?
Public transportation is, of course, the best way to get around Chicago, not just because it is the most affordable, but it is also simple to use and navigate through. The Chicago Transit Authority (CTA) operates the city's transportation system and has routes covering almost all the attractions.
Travelers can choose the L Train (Union Station is also a sight to see), which is the best option, the bus, or Metra Rail to reach various destinations.
Taxis, water taxis, and cars are other options to consider. Taxis are perfect for travelers looking to get to destinations beyond downtown Chicago. A cheaper alternative is ridesharing via Uber or Lyft.
Vacationers can also use water taxis along the Chicago River and Lake Michigan to get to some of the most popular areas in the city, including the Museum Campus and Chinatown.
Vacationers planning to get around Windy City in cars should prepare for hefty parking costs, and heavy traffics, especially during peak hours.
Q: What is Chicago famous for?
Windy City is famous having the best 20th-century art and architecture, plus some of the most impressive attractions, including the Navy Pier, Millennium Park, The Adler Planetarium, and the Art Institute Of Chicago.
Q: Is Chicago worth visiting?
There is so much to experience in Chicago, and every traveler is going to relish their trip. From a fantastic arts scene to incredible dining to world-class hotels offering various accommodation options to choose from, Windy City is definitely worth visiting.