Introduction

Hey there, future Chicago explorers! Are you ready for an awesome adventure in the Windy City? This 2- day Chicago itinerary is packed with fun things to do in Chicago that will make your trip unforgettable. You’ll get to explore Chicago's amazing skyline, delicious deep-dish pizza, and vibrant culture. Imagine taking a stroll along the beautiful Lake Michigan, visiting the famous Art Institute, and checking out the thrilling ride at Navy Pier! With so many cool places to discover and tasty treats to try, you’ll be making memories that will last a lifetime. So grab your backpacks and let’s dive into this exciting Chicago adventure!

Overview

• Day 1: Discover the Heart of Chicago with breathtaking views from Willis Tower and iconic art at Millennium Park and the Art Institute of Chicago.
• Day 2: Experience a Taste of Chicago Culture with scenic views at Navy Pier, fascinating history at the Field Museum, and a picturesque boat tour along the Chicago River.

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Detailed Itinerary

Day 1: Discover the Heart of Chicago

Start your day by visiting the iconic Willis Tower. Make your way to the Sky Deck for breathtaking views of the city skyline. Arrive early to avoid long lines and enjoy the thrill of standing on the glass ledge that extends out 1. 353 feet above the ground.

After taking in the views, head to the Art Institute of Chicago for a dose of culture. This museum is home to an impressive collection of Impressionist and Post- Impressionist masterpieces. Spend a few hours wandering through the galleries and be sure to check out Grant Wood's famous painting, "American Gothic."

In the afternoon, take a stroll through Millennium Park. Don’t forget to snap a selfie with the famous Cloud Gate sculpture, affectionately known as "The Bean." The park is also a great spot for lunch, with several eateries nearby offering delicious options.

Tips for Day 1:

• Book your Sky Deck tickets in advance to save time.
• Wear comfortable shoes, as you'll be walking a lot.

Day 2: Embrace the City’s Culture and Cuisine

On your second day, start with a visit to the historic Navy Pier. Enjoy the waterfront views and perhaps take a ride on the Ferris wheel. You can also explore the various shops and grab a coffee at one of the charming cafes.

Afterward, make your way to the Field Museum to learn about natural history. The museum houses an extensive collection of artifacts, including Sue, the famous T. rex skeleton. Plan to spend a few hours here to fully appreciate the exhibits.

For lunch, experience a classic Chicago deep- dish pizza at Giordano's. This local favorite is known for its delicious stuffed pizza, making it a must-try during your visit. After lunch, you can unwind by exploring the Chicago Riverwalk, where you can take in the architecture and perhaps enjoy a boat tour.

Tips for Day 2:

• Arrive early at Navy Pier to avoid crowds.
• Consider booking a boat tour in advance for a better experience.

Before You Go

Best Time to Visit

Chicago is a city that offers distinct experiences throughout the year. The best time to visit is during the spring (April to June) and fall (September to October) when the weather is mild, and the city is less crowded.

Summer can be hot and humid, but it's also when many festivals and events take place, including the famous Chicago Air and Water Show.

How to Get There

Chicago is accessible via two major airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). Both airports serve numerous domestic and international flights, making it easy to reach the city.

For driving, Chicago is conveniently located at the intersection of several major highways, including I- 90 and I-55.

Transportation Options

Once in the city, various transportation options are available to help you get around. The Chicago Transit Authority (CTA) operates an extensive bus and train system that is both affordable and efficient.

Other options include ride- sharing services like Uber and Lyft, as well as bike rentals and taxis. You can also explore the city on foot, especially in areas like downtown and the Magnificent Mile.

SIM Cards

If you need mobile data during your stay, consider purchasing a local SIM card. Major providers like T- Mobile and AT&T offer prepaid options that are easy to set up.

You can buy SIM cards at the airport, convenience stores, or electronics shops. Make sure your phone is unlocked before you arrive.

Visas

Check if you require a visa to enter the United States. The U.S. Department of State visas.html) provides information on visa requirements and application procedures.

Most visitors from certain countries may qualify for the Visa Waiver Program.

Typical Weather

Chicago experiences four distinct seasons, with cold winters and hot summers.

• Winter (December to February): Average temperatures can drop below freezing.
• Spring (March to May): Mild temperatures and blooming flowers.
• Summer (June to August): Hot and humid with temperatures often exceeding 85°F (29°C).
• Fall (September to November): Crisp air and beautiful fall foliage.

Budget Tips

Chicago can be enjoyed on various budgets. To save money:

• Use public transportation instead of taxis.
• Look for free events and festivals, especially in the summer.
• Consider staying in budget accommodations or hostels.

Dining at local eateries or food trucks can also provide tasty options without breaking the bank.

Safety Considerations

Chicago is generally safe for tourists, but like any major city, it's essential to stay aware of your surroundings.

• Stick to well-lit areas at night.
• Avoid displaying expensive items.
• Use reputable transportation services.

Following these tips can help ensure a safe and enjoyable visit to the Windy City.

Where to Stay

Budget

• HI Chicago Hostel - This hostel is perfect for travelers looking for an affordable stay. Located near the Grant Park area, it offers dormitory-style accommodations as well as private rooms. Guests enjoy a communal kitchen and social events, making it a great place to meet fellow travelers.

• The Willows Hotel - Situated in Lincoln Park, this budget-friendly hotel is known for its charming décor and cozy atmosphere. It offers easy access to public transportation and local attractions like the Lincoln Park Zoo, making it an ideal choice for budget-conscious visitors.

Mid-Range

• Holiday Inn Chicago Mart Plaza - This hotel boasts stunning views of the Chicago River and downtown skyline. With spacious rooms and a rooftop bar, it provides a comfortable stay at a reasonable price. Its central location allows easy access to shopping and dining in the River North area.

• The Talbott Hotel - Located in the upscale Gold Coast neighborhood, this boutique hotel combines modern amenities with classic elegance. Guests appreciate the proximity to high-end shopping on Michigan Avenue, as well as the charming local restaurants nearby.

Luxury

• The Langham, Chicago - This luxurious hotel sits along the Chicago River and is renowned for its exceptional service and lavish accommodations. The on-site spa and fine dining restaurant elevate the experience, making it a top choice for travelers seeking indulgence in the heart of the city.

• The Peninsula Chicago - Known for its opulent rooms and world-class service, The Peninsula offers a rooftop pool and a renowned spa. Located in the Magnificent Mile area, it’s perfect for those who want to enjoy high-end shopping and dining just steps away from their hotel.

Where to Eat

Lou Malnati's Pizzeria

No trip to Chicago is complete without indulging in a deep- dish pizza from Lou Malnati's. This iconic pizzeria is famous for its buttery crust, rich tomato sauce, and a generous layer of gooey mozzarella cheese. Be sure to try the "Malnati Chicago Classic" topped with sausage, as it's a local favorite.

Portillo's

For a true taste of Chicago- style hot dogs, head to Portillo's. This fast-casual chain serves up Chicago-style hot dogs that are loaded with all the traditional toppings, including yellow mustard, relish, onions, tomato, pickles, and sport peppers—all served on a poppy seed bun. Don't forget to pair your meal with their famous Italian beef sandwich!

The Purple Pig

The Purple Pig offers a unique dining experience with a focus on Mediterranean- inspired small plates. Known for its charcuterie and cheese offerings, you must try the "Pig's Ear" with fried egg and the "Pork Shoulder" with creamy polenta. This bustling eatery also features a great selection of wines that perfectly complement the dishes.

Giordano's

Another staple for deep- dish pizza lovers, Giordano's is renowned for its stuffed pizza. The crust is filled with layers of cheese and your choice of toppings, then topped with a zesty tomato sauce. Their "Stuffed Spinach" pizza is a must-try for a unique twist on this Chicago classic.

Eataly

For those who want to explore a variety of Italian cuisine, Eataly is the perfect destination. This vibrant marketplace offers numerous restaurants and food counters where you can sample fresh pasta, pizza, and gelato. Don't miss out on their "Pasta alla Puttanesca" and the delightful array of pastries.

Chicago French Market

Located in the West Loop, the Chicago French Market is an indoor market that features a variety of food vendors. You can find everything from artisanal cheeses to gourmet sandwiches. Make sure to try the "Duck Confit" from one of the vendors and enjoy the lively atmosphere while you eat.

These dining spots showcase the rich culinary scene in Chicago, offering a mix of iconic dishes and unique flavors that are sure to satisfy any palate.

Local Tips for Chicago

Exploring Chicago can be an exciting adventure, especially for first- time visitors. Here are some essential tips to make your trip smooth and enjoyable.

Currency

• The currency used in Chicago is the United States Dollar (USD).

• Credit and debit cards are widely accepted, but it’s a good idea to carry some cash for smaller purchases.

• ATMs are available throughout the city, but be aware of potential fees from your bank.

Customs

• Chicagoans are generally friendly and helpful, so don’t hesitate to ask for directions or recommendations.

• When dining, it's customary to greet your server and say thank you when leaving.

• Public transportation etiquette includes giving up your seat to elderly passengers and keeping your voice down.

Local Scams to Avoid

• Be cautious of street performers asking for money; while many are legitimate, some may be aggressive in their requests.

• Watch out for individuals asking for donations or selling items near tourist attractions, as some may not be legitimate.

• If someone approaches you with a "lost" or "broken" story, be skeptical and prioritize your safety.

Safety

• Chicago is generally safe, but like any major city, it’s essential to stay aware of your surroundings.

• Stick to well-lit, populated areas, especially at night.

• If you're using public transportation, keep your belongings secure and be mindful of your surroundings.

Tipping

• Tipping is customary in Chicago. For restaurants, a 10-20% tip is standard.

• For taxis, rounding up to the nearest dollar or adding 10-15% is appreciated.

• Consider tipping hotel staff, such as bellhops and housekeeping, for good service.

Helpful Apps

• Google Maps: Essential for navigation and finding public transportation options.

• Transit App: This app provides real-time updates on public transport schedules.

• Yelp: Use this app to find and review local restaurants and attractions.

• Uber/Lyft: Rideshare apps are convenient for getting around the city quickly.

With these tips in mind, you’ll be well- prepared to enjoy the Windy City!

Frequently Asked Questions About Chicago

What are the must- see attractions in Chicago?

Chicago is home to many iconic attractions that should be included in your Chicago itinerary. Don't miss the stunning views from the Willis Tower Skydeck, where you can step out onto the glass ledge. Another must- see is Millennium Park, famous for its Cloud Gate sculpture, known as "The Bean." For those interested in art, the Art Institute of Chicago boasts an impressive collection, including works by Grant Wood and Georgia O'Keeffe. Exploring Navy Pier is also a favorite among visitors, featuring rides, restaurants, and beautiful lakefront views.

What is the best time to visit Chicago?

The best time to visit Chicago is during the spring and fall when the weather is mild and pleasant. Spring brings blooming flowers and outdoor festivals, making it a great time for sightseeing and enjoying the many things to do in Chicago. Fall showcases vibrant foliage and events like the Chicago Gourmet Festival. However, if you enjoy winter sports and holiday festivities, visiting in winter can also be delightful, especially with attractions like the Christkindlmarket and ice skating in Millennium Park.

How can I get around Chicago?

Getting around Chicago is easy thanks to its extensive public transportation system. The Chicago Transit Authority (CTA) operates buses and trains that connect you to most attractions on your Chicago itinerary. Alternatively, rideshare services like Uber and Lyft are widely available. If you prefer cycling, consider renting a bike through the Divvy bike- sharing program, which offers a fun way to explore the city while enjoying its many bike paths.

What food should I try in Chicago?

When in Chicago, you must try the famous deep-dish pizza, a local specialty that is sure to satisfy your cravings. Other culinary delights include Chicago-style hot dogs, which are loaded with toppings and served without ketchup, and Italian beef sandwiches, known for their flavorful, juicy meat. Be sure to explore the diverse dining scene in neighborhoods like Pilsen and Wicker Park for a broader taste of local flavors, making your trip unforgettable with every bite.

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