Are you looking to book your very first trip to Chicago? In this first-timer guide, we share the perfect 3-days in Chicago itinerary. Use this guide to help you book an epic trip to the Windy City.
3 Days in Chicago Itinerary Introduction
Visiting Chicago for the first time, especially in the summer, is love at first sight. With truly the most beautiful skyline in the United States, the iconic riverwalk, some of the best food a city can offer, and endless attractions, Chicago deserves its title as one of the best cities in the world.
In this Chicago itinerary, we’ll share everything you need to know to make your first trip successful. We’re covering how to ride the L train from the airport to downtown. Plus, where to stay, what to eat, and must-visit attractions in three days.
3 Days in Chicago Itinerary: Getting from O’Hare to Downtown Chicago on the L Train
If you’re planning your first trip to Chicago, one of the best tips is to skip the rental car. This one decision can save you hundreds of dollars on your trip. Plus, Chicago has some of the best and most reliable public transportation in the country.
When planning your 3 days in Chicago, it’s good to know that the city is fourth most walkable city in the U.S. It also ranks in the top five for its efficient public transportation system. As first-time visitors ourselves, we found Chicago’s train system easy to navigate from the airport and back. It is hands-down the most affordable way to get around town.
Once you land at O’Hare International Airport, follow the blue signs that read “Train to City.” These will guide you to the Blue Line Station of the iconic Chicago ‘L’ Train. This line takes you directly from the airport into the Downtown Loop area.
You’ll find ticket kiosks at the station where you can purchase a Ventra card for just $5. There’s also a super user-friendly Ventra app. Use this app to reload cash, check train times, and see real-time updates on delays.
And don’t worry, you won’t be the only traveler on the Blue Line. There are always plenty of people with luggage, and we felt completely safe on this line. That said, it’s still a good idea to travel during daylight hours.
L Train vs Uber Cost Comparison
Taking the train instead of a car or rideshare is not only convenient but also budget-friendly. A one-way Uber from the airport to downtown Chicago averages $50 or more, depending on the time of day. In comparison, hopping on the Blue Line costs around $5. If you’re sticking to a budget or want to spend more money, this is the best route.
Before you hop on board, give your hotel a quick call to find out which stop is closest to your stay. If you’re booked anywhere in or near the downtown area, you’ll likely be within walking distance of Chicago’s top attractions.
3 Days in Chicago Itinerary: Where to stay | Kimpton Gray Chicago
For our 3 days in Chicago, we stayed at the Kimpton Gray Hotel. This is a stunning boutique property located in the city’s Financial District. The hotel is located inside a historic building. It once served as the Midwest headquarters of the New York Life Insurance Company.
Kimpton Gray has beautiful Art Deco architecture with modern luxuries. We stayed in a King Suite, which was incredibly spacious. The room featuring a stylish bathroom and one of the comfiest beds we’ve ever slept in.
The hotel also has thoughtfully designed common areas. It includes cozy seating for enjoying the complimentary morning coffee and tea. Plus, a kid-friendly corner with board games and coloring sheets if you’re traveling with kids like us. There are also three restaurants, bars/ lounges, and even a Starbucks on site.
One of the things I loved most about this property was the walkability. The financial district is very centralized. It is just a 10-minute walk from many of the top spots on your Chicago itinerary. We walked daily to the riverwalk, Willis Tower, Millennium Park, and more.
3 Days in Chicago Itinerary
Day 1 of 3 days in Chicago itinerary:
Skydeck at Willis Tower:
One of the highlights on day one of our Chicago itinerary was a visit to the Skydeck at Willis Tower. It was the perfect way to kick off the trip. We redeemed our C3 Pass by CityPASS here, which saved time and money on multiple attractions throughout the city. Before heading to the top, we took our time exploring the exhibits that walk you through Chicago’s history. Learn about everything from its early roots and iconic architecture to its deep-dish pizza, music scene, and famous hometown celebrities. The displays were interactive and engaging. This is perfect for first-time visitors to get familiar with the city’s culture.
After the exhibits, we hopped on the elevator up to the Skydeck itself. There were panoramic views of the iconic Chicago’s skyline. If you’re feeling brave, you can even step out onto The Ledge that extends over the city streets below. It’s a bucket list experience and a must-do for any first-timer spending 3 days in Chicago.
Dinner at the Hotel | La Bella’s Chicago:
If you’re staying at the Kimpton Gray, La Bella’s is a great hotel option for dining on your first night. This is a delicious Italian bistro with favorites like pizzas, pastas, meatballs. They also have unique fusion dishes like the Nashville hot chicken bao buns. The restaurant has a great ambiance with indoor and outdoor seating.
Day 2 of 3-day Chicago Itinerary
Breakfast at Starbucks Reserve Roastery Chicago:
Chicago is home to the world’s largest Starbucks, and it’s called the Reserve Roastery. This roastery is a 5-level experience with things from a cocktail bar to an experimental coffee bar . There are two levels with snacks and elevated food items like gourmet pizza, sandwiches, desserts, and more. There’s even a rooftop lounge area where you can take your coffee and enjoy the view of the Magnificent Mile.
Not only does this place have stunning architecture, but it’s functional as well. You can literally see the coffee beans being transported between floors. If you’re a coffee lover or foodie, this place is a must-do when visiting an exploring Magnificent Mile.
Sightseeing at Millennium Park and Cloud Gate “Chicago Bean”:
Can you really say you’ve been to Chicago without visiting Millennium Park and the Bean? Visiting one of Chicago’s most iconic attractions is completely free. Its also within walking distance of the Riverwalk and most downtown Chicago hotels. There are a number of delicious restaurants and even a food hall right below the “Cloud Gate”. So, this is a great spot to grab lunch or take a stroll.
During the summer months, don’t forget to pack a swimsuit. Millennium Park is home to the Chicago Crown Fountain, which is a fun and free water attraction especially for kids.
World’s First Nutella Cafe’: World’s First Nutella Cafe’:
The Chicago location is Nutella Cafe’s first in the world and America’s only current location. It’s located on Michigan Avenue and within walking distance of some of Chicago’s best attractions. You can literally put Nutella on just about anything.
There’s an extensive menu of items to choose from. You can also make a souvenir jar customized with your name on it. Expect to pay around $10 per item, give or take. This place is tiny, and the lines can get pretty long. While there is seating both indoors it gets crowded. So, I recommend going earlier in the day or preparing to take your items to go. If you’re a Nutella Superfan, I highly recommend going.
Chicago Pizza Dinner at Giordano’s:
No first trip to Chicago is complete without a classic deep-dish Chicago-style pizza. Giordanos is one of Chicago’s legendary pizza places. They have been serving stuffed deep dishes and other Italian favorites since 1974.
Giordano’s was founded by Italian immigrant brothers who brought their mother’s famous “Italian Easter Pie” recipe to Chicago. Today, the restaurant is famous around the world. There are multiple locations all over the city. So, it’s an easy and delicious stop to grab dinner after a day of exploring.
Day 3 of 3-Day Chicago Itinerary
Brunch/ Lunch at Restoration Hardware’s 3 Arts Cafe:
Did you know that you could eat at certain Restoration Hardware locations? Brunch at the 3 Arts Club at Chicago’s Restoration Hardware is not to be missed. There are 20 locations across the US and Europe, and not only are they stunning, but the menus are phenomenal. At 3 Arts Club Cafe, some of the must-try menu items are the lobster roll with fries and house sauce. Also, the shaved Ribeye on garlic bread with Au Jus sauce.
The 3 Arts Cafe is not located downtown; it’s actually in the picturesque Streeterville neighborhood, and it is worth the drive or Uber to check out.
Here are three tips for your visit to any location:
- Make your reservations EARLY! The books typically open up 30 days in advance on OpenTable
- Expect to pay for the experience. We spent $125 on brunch/lunch with no alcohol. It’s expensive but an amazing experience.
- Pay attention to the menu. Some items are seasonal and will change based on when you visit and the location.
Chicago’s Shedd Aquarium:
Chicago’s Shedd Aquarium is one of the must-visit attractions on Chicago’s Museum Campus. It’s a great place for families and nature lovers alike to visit. This place is massive with over 32,000 animals and interactive exhibits. Plan to spend hours here exploring and learning about both local animals and ones from around the world.
General admission for non-Chicago residents is $39.95 for adults and $29.95 for children aged 3–11. However, if you purchase the C3 Chicago City pass, it is one of the museums included in the visit. To make the most of your visit, plan to arrive at least four hours before closing; the aquarium operates from 9:00 AM to 5:00 PM daily.
After leaving the aquarium, be sure to stick around and explore the museum campus. The campus has a 57-acre park and shoreline walk with a striking view of the Chicago skyline. This is a great place for a picnic or an afternoon walk.
Visit Garrett’s Popcorn:
Before hopping on the Chicago Architecture Tour, be sure to grab a snack at another Chicago staple, Garrett’s Popcorn. They are known worldwide for their famous Chicago mix that blends savory cheddar with sweet caramel. This place has been a Chicago staple since 1949. It’s the perfect snack for your trip down the riverwalk or if you want to indulge in something delicious.
Chicago Architecture Tour:
Chicago has some of the most unique architecture in the United States. The best way to see it and learn about it is from the Chicago riverfront. The tour was a 75-minute-long guided tour. The guide was funny and informative, and we learned about 45 iconic Chicago landmarks and how they came to be. Shoreline offers two pickup locations, one on Michigan Avenue and the other on the Navy Pier. You pick your location.
The cost is around $50 per person. However, we got the most of our money by booking a C3 Chicago pass with the My City pass bundle. There is a bathroom and bar for on the lower deck. I highly recommend going on this tour around 7 pm because you get the best of day and nighttime views.
Dinner at Nobu Chicago:
If you love high-quality Japanese cuisine, sushi, and stunning aesthetics, Nobu Chicago is one of the best places to enjoy fine dining. This world-renowned Japanese-Peruvian fusion restaurant is located in the trendy West Loop and offers beautifully crafted dishes. Some of the dishes that we love and highly recommend are the Black Cod Miso, cut sushi rolls, and more. Nobu is known for its incredible service. Their offerigs are high quality with sleek + modern vibes. This is the perfect place to enjoy your last dinner in the city.
Dessert at Jeni’s Ice Cream:
After leaving Nobu, walk over to Jeni’s Ice Cream for the perfect scoop or two. Jeni’s has some of the best ice cream with a perfectly creamy texture and unique flavors. Though they were not originally founded in Chicago, they are well-loved by the locals and midwesterners in general. There are multiple locations around the city to check out, and it’s well worth the wait.
The perfect first-timer 3 days in Chicago itinerary: Conclusion
There you have it, the perfect 3-day Chicago itinerary. Chicago is a huge city with so much to offer on a trip, and it is impossible to see, do, eat, or explore it all on a 3-day weekend trip. However, this is a starter pack for exploring, eating, and seeing as much as you can on foot for your first time in the city.
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