Planning a trip to Chicago? Whether it’s your first time visiting or you’re returning to rediscover the city’s charm, this 3-day itinerary will guide you through the best Chicago has to offer.
With its rich history, iconic architecture, and vibrant food scene, Chicago is a city that promises something for everyone. Let’s dive into how to make the most of your weekend in the Windy City.
What to Know Before You Go
Best Time to Visit
Chicago is a city that shines in all seasons, but the best times to visit are during the spring (April to June) and fall (September to early November). During these months, the weather is mild and perfect for exploring. If you’re not bothered by the cold, December offers a magical experience with the city decked out in holiday lights.
Where to Stay
Choosing the right neighborhood is key to enjoying your stay. For first-timers, the Magnificent Mile is ideal, offering easy access to shopping, dining, and major attractions. Other great areas include The Loop, perfect for those who want to be near Millennium Park and Cloud Gate, and River North, close to Navy Pier. If you prefer a more luxurious stay, the Gold Coast is a top choice, while South Loop is ideal for museum lovers.
Getting Around
Chicago is known for its efficient public transportation. The city’s metro, known as the “L” train, and bus systems are the fastest ways to get around. If you’re new to the city, consider the Hop-On Hop-Off Bus Tour to get acquainted with the major sights. Chicago is also very walkable, but be prepared to take a cab, Uber, or public transit between attractions, as some distances can be significant.
Day 1: Iconic Sights and Deep Dish Delights
Morning: Skydeck Chicago
Start your trip with a visit to Skydeck Chicago at the Willis Tower. Arrive early to avoid the crowds and take in the breathtaking views from 1,353 feet above the ground. On a clear day, you can see four states from this vantage point. If you’re planning to catch the sunset, aim to arrive 30-60 minutes before sunset time.
Mid-Morning: Art Institute of Chicago
Next, head over to the Art Institute of Chicago, a must-visit for art lovers. With a collection that includes works by Van Gogh, Monet, and Seurat, this museum is often ranked as one of the best in the world. Spend a couple of hours here, and don’t forget to use the Chicago CityPASS for expedited entry and additional savings.
Afternoon: Millennium Park and The Loop
After exploring the Art Institute, take a leisurely stroll to Millennium Park to see the famous Cloud Gate, affectionately known as “The Bean.” This area is great for a lunch break, with plenty of cafes and the Plaza at Park Grill offering casual dining and live music.
Evening: Deep Dish Pizza
No trip to Chicago is complete without indulging in its legendary deep dish pizza. While Lou Malnati’s is a popular choice, many locals swear by Uno’s and Due’s. Take your pick and enjoy a hearty meal to end your first day in Chicago.
Day 2: Museums, Shopping, and Skyline Views
Morning: Shedd Aquarium and Field Museum
Kick off your second day with a visit to the Shedd Aquarium, the world’s largest indoor aquarium. Plan to spend a couple of hours here exploring its diverse exhibits. Afterward, head over to the Field Museum, a treasure trove of natural history. Highlights include Sue the T-Rex and the Evolving Planet exhibit.
Afternoon: Grant Park and Magnificent Mile
Grab lunch to-go and enjoy it in Grant Park, where you can relax and take in views of Chicago’s skyline and Lake Michigan. Afterward, make your way to the Magnificent Mile for some shopping. Whether you’re browsing the high-end boutiques or checking out the iconic Water Tower Place, this area has something for every shopper.
Evening: 360 Chicago Observation Deck
End your day with a visit to the 360 Chicago Observation Deck. Located on the 94th floor of the John Hancock Building, this deck offers stunning nighttime views of the city. For the adventurous, try the Tilt attraction, which tilts you out over the city from the top of the building. If you prefer a more relaxed experience, enjoy a drink at the Signature Lounge on the 95th floor.
Day 3: Parks, Neighborhoods, and Culture
Morning: Lincoln Park Zoo and Conservatory
Start your final day at the Lincoln Park Zoo, one of the oldest zoos in the country with free admission. Nearby, the Lincoln Park Conservatory is a beautiful botanical garden that’s open year-round, offering a peaceful escape from the city’s hustle and bustle.
Afternoon: Wicker Park and Gold Coast
After exploring Lincoln Park, hop on public transit to Wicker Park, a trendy neighborhood known for its vintage shops and boutique stores. It’s a great spot to grab lunch and enjoy the local vibe. Next, head to the Gold Coast, an affluent neighborhood known for its historic homes and designer shops. If you’re a foodie, consider joining a food tour to sample some of Chicago’s best bites.
Evening: A Night on the Town
For your final night, you have several great options. Sports fans can catch a game at Wrigley Field, while music lovers can enjoy live blues at iconic venues like Andy’s Jazz Club or Blue Chicago. If you’re more into theater, check out a show through Broadway in Chicago, which offers top-tier performances at a fraction of New York prices. For something more laid-back, try your hand at 10pin Bowling Lounge or unwind at one of Chicago’s many lounges and bars.
Insider Tips from a Local:
As a resident of the Chicago area, I agree with most of the recommendations listed here. However, I’d like to add a few of my own:
Walking vs. Transit
Chicago is a fantastic city for walking, especially during the warmer months, but be mindful that some attractions are spread out. Consider using cabs, Uber, or public transportation to save time and energy. The Pedway, an underground pedestrian walkway, is also a great option during the winter or on rainy days.
Navy Pier: A Word of Caution
While Navy Pier is often recommended to tourists, many locals find it overly commercialized. By all means, enjoy the Ferris wheel, visit the children’s museum, or take a boat ride, but don’t plan to spend your entire day there. Chicago has much more to offer beyond this tourist hotspot.
Deep Dish Debate
When it comes to deep dish pizza, opinions are divided. While Malnati’s is often praised, many locals prefer the pies at Uno’s and Due’s. Try them all and decide for yourself!
Broadway in Chicago
Chicago’s theater scene is thriving, and Broadway in Chicago offers performances that rival those in New York City, often at lower prices. Discounted tickets are also available for some shows, making it a great way to enjoy a night out without breaking the bank.
Don’t Overlook Adler Planetarium
Often overshadowed by its flashier neighbors in the Museum Campus, Adler Planetarium is a gem for anyone interested in astronomy and space. It’s definitely worth a visit, especially if you’re looking for something a bit different.