Chicago Travel Guide…
Whether you're a history buff, an art enthusiast, or a foodie, Chicago has something for everyone!
I lived in Chicago when I started my career as a flight attendant… and quickly fell in love with the “Windy City”! I lived near the Navy Pier in a one-bedroom convertible with 4-5 flight attendants (typical living arrangements for new flight attendants who are poor). There are so many crazy stories… I’ll share a G-rated memory: I ran my own personal marathon in Chicago. I was having a good running day so I kept running. I’m a slow runner and was gone 5 hours, so my roommate was worried I was dead in a ditch and had all of our friends out looking for me (this was before cell phones). I was fine, I had a good running day and was enjoying the beautiful running path along Lake Michigan. 😆
Getting from the Airport to Downtown Chicago:
You can get to downtown Chicago from Chicago’s Midway Airport and O’Hare International Airport on the ‘L’ Train. Midway Airport has a walkway to the train station. It takes 30 minutes to reach downtown on the Orange Line (I was based at Midway Airport). Travel time from O’Hare on the Blue Line to downtown is 40-45 minutes.
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Here’s my list of must-see places to ensure you make the most of your visit to this iconic city!
Mobster Tours:
Chicago was a playground for mobsters and had a long history of organized crime. It was home to the famous mafia figure Al Capone. Take a tour to learn about Chicago’s bloody past:
Gangsters and Ghosts Guided Walking Tour
Movie Tour:
Private Guided Tour of Chicago Suburbs Movie Sites: Take a peek into the garage from Ferris Bueller’s Day Off, and drive by the McCallister House from the movie Home Alone.
TIP: Save up to 48% on 5 Top Attractions with the Chicago CityPASS!
Millennium Park:
Begin your journey at Millennium Park, a sprawling urban oasis. The park hosts various art installations, events, and beautiful gardens. What to do in Millennium Park:
Cloud Gate (The Bean):
Marvel at the iconic Cloud Gate sculpture, affectionately known as "The Bean." It captures unique reflections of the city skyline on its polished surface. Make sure you walk around and below it to experience “The Bean”.
Crown Fountain:
The Crown Fountain is a pair of interactive video sculptures featuring the changing faces of Chicago residents. It's a great spot for families, especially during the warmer months when kids can splash around in the shallow reflecting pool.
Jay Pritzker Pavilion:
Check the schedule for events at the Jay Pritzker Pavilion, an architecturally stunning outdoor concert venue. From music festivals to performances by the Grant Park Orchestra, there's always something happening at this venue.
Lurie Garden:
This beautifully landscaped garden showcases a variety of plants, providing a peaceful retreat from the city.
❄️ During the winter visit the Millennium Park Ice Skating Rink. Admission is free but online tickets are required. Ice skates can be rented.
Art Institute of Chicago:
Delve into the world of art at the renowned Art Institute of Chicago. Home to an extensive collection of masterpieces, including works by Van Gogh and Grant Wood. Buy your tickets here.
Grant Park:
Discover the beauty of Grant Park, Chicago's "front yard." This expansive green space hosts various festivals and events, making it ideal for a leisurely picnic or a relaxing afternoon stroll.
Visit Buckingham Fountain, one of the largest fountains in the world. The design was inspired by a fountain at the Palace of Versailles in France.
Museum Campus:
Nature and science enthusiasts should explore the Museum Campus, home to the Shedd Aquarium, Adler Planetarium, and the Field Museum. Immerse yourself in marine life, astronomy, and natural history all in one place.
The Palmer House:
The Palmer House Hilton, located in downtown Chicago, is a historic hotel that has been an integral part of the city's landscape since 1871.
Lobby and Peacock Door:
Step into the lobby adorned with intricate decor and the famous Peacock Door, crafted by Louis Comfort of Tiffany.
Art Collection:
Explore the impressive art collection within the hotel, featuring over 50 pieces of original art. The collection includes paintings, sculptures, and decorative arts.
Afternoon Tea at the Lobby:
Indulge in the tradition of afternoon tea at the Palmer House's lobby. Try a selection of teas, finger sandwiches, and pastries while surrounded by elegant surroundings.
Willis Tower Skydeck:
Take in breathtaking panoramic views of the city from the glass-floored observation deck called “the Skydeck” on the 103rd floor. An elevator reaches the top in only 60 seconds offering a unique perspective of Chicago's skyline. You’ll have some of the best photo opportunities in the city with views extending to four states. There’s also the Ledge, a glass balcony extending four feet outside Willis Tower.
Tip: Go in the morning or towards the end of the day to avoid crowds.
Chicago Cultural Center:
This architectural gem hosts free concerts, exhibitions, and events. It’s free to walk inside. Once a library, it’s home to two stained-glass domes including the largest Tiffany dome in the world. The building has free tours Wednesday-Saturday at 1:15 pm.
Macy’s on State:
Macy's on State Street, located in the heart of downtown Chicago, is an iconic and historic department store. Originally known as Marshall Field's. This is a designated Chicago Landmark. Highlights to explore at Macy's on State:
Great Clocks:
Admire the Great Clocks on the corner of State and Washington Streets. These clocks are a popular meeting spot and have been a distinctive feature of the building since 1897.
Tiffany Ceiling:
Macy's Tiffany Dome Ceiling uses Favrile glass, built in 1907. It also happens to be the largest glass mosaic of this style. It contains over 1.6 million pieces.
Walnut Room:
Enjoy a meal at the historic Walnut Room on the 7th floor. Known for its classic American cuisine and for being the first restaurant in a department store.
❄️This restaurant is especially popular during the holiday season, featuring a large, beautifully decorated Christmas tree.
❄️ State Street Window Displays:
During the holiday season, don't miss the window displays along State Street. Macy's transforms its windows into festive scenes, adding to the magical ambiance of downtown Chicago.
Macy's Culinary Studio:
Participate in culinary events and classes at the Macy's Culinary Studio. Learn from expert chefs and enjoy a hands-on experience.
Shopping:
Explore the 8 floors of retail space at Macy’s on State. This Macy’s also offers Historical Store Tours.
❄️ If you collect travel ornaments, I always find the most beautiful ornaments at Macy’s.
The Daley Center:
Picasso Sculpture:
Explore the Daley Plaza to view the Picasso sculpture, officially titled "Untitled" but commonly referred to as the "Daley Plaza Picasso."
The Richard J. Daley Center is a government building open to the public during normal business hours. If you're willing to go through the security check, you're welcome to ride the elevator upstairs to the 25th floor. You’ll get FREE views of (one side) of the Loop skyline and lakefront from the very heart of the city.
❄️ Christmas Market at the Daley Center: Christkindlmarket Chicago.
Shop with over 50 vendors from around the world, from November 17 - December 24. Try Gluhwein: a mulled, spiced, red wine served in a mug. They also have non-alcoholic versions and hot chocolate. It comes in the annual souvenir mug.
Chicago Theater:
The Chicago Theatre is a historic venue that opened its doors in 1921 and is located in the heart of the city's Loop district. The marquee is a popular destination for pictures, but you can also attend live performances from Broadway shows and concerts to comedy acts. Click here to see their schedule and buy tickets.
Chicago Riverwalk:
Take the scenic path along the Chicago River, admire the architecture, and grab a bite at one of the riverside cafes. The Chicago Riverwalk is a 1.25-mile path that follows the banks of the Chicago River from Lake Shore Drive to Lake Street. This is where I lived in Chicago. 🙌 It’s one of my favorite walking paths in the city! The views are breathtaking!
Chicago has some of the best kayaking in the Midwest. Wateriders Kayak Tours offers several different tours ranging from an architecture tour, moonlight paddle, ghosts and gangsters tour, Navy Pier Fireworks Paddle and more.
Chicago River Architecture Cruise:
Take an Architecture River Cruise to explore the city’s skyline and learn about its rich architectural history. It’s a great way to see the city while learning about the buildings. This is one of the most popular tours in Chicago.
Navy Pier:
For a blend of entertainment and scenic views of Lake Michigan, head to the Navy Pier. Visit Centennial Wheel, soaring to heights of 200 feet with 360-degree views of Chicago and Lake Michigan. Go on carnival rides, and try authentic Chicago food in one of the most iconic venues in the city. Explore the sights of Chicago on a cruise on Lake Michigan. They offer elegant dining cruises, sightseeing cruises, or a thrilling ride on Seadog. Don’t miss the fireworks show on Wednesday nights at 9 pm and Saturday nights at 10 pm from Memorial Day weekend through Labor Day Weekend.
Lakefront Trail:
The Lakefront Trail is an 18-mile path along Lake Michigan. Rent a bike and enjoy the views! The last time I was there I rented a bike from Bike and Roll Chicago at Navy Pier.
Bike Tours:
Lakefront Neighborhoods Bike Tour: Chicago has beautiful neighborhoods with amazing architecture. Take this tour to have a peek and see some hidden gems.
Chicago Bikes, Bites, and Brews Biking Tour: Sample foods from Chicago’s four favorite food groups: pizza, hot dogs, brownies, and beer on this city bike tour.
Magnificent Mile:
Michigan Avenue features high-end boutiques, department stores, restaurants, and the world’s largest Starbucks. Take a stroll, shop for souvenirs, and enjoy the vibrant cityscape. The Magnificent Mile is a nickname for North Michigan Avenue. The Wrigley Building marks the beginning of the Magnificent Mile and the John Hancock Center is found near the end of the shopping district.
My daughter’s favorite store is the American Girl Place Chicago. After finding the perfect doll we stopped at the salon to get her doll’s hair braided. Then we went to the American Girl Cafe for lunch. Her new American Girl joined us for lunch. It was an experience she’ll never forget!
360 Chicago Observation Deck:
Visit the observation deck for amazing views on the 94th floor. This experience is $30.00 for adults & $20.00 for youth. You can also visit CloudBar, where you can enjoy some of the best views in the city over drinks and snacks. You can try the Tilt, an enclosed glass and steel moveable platform. It will slowly tilt outward with a downward-facing view of Chicago. Open 9 am to 11 pm. Click here for tickets.
Oak Street Beach:
Oak Street Beach is a popular and scenic lakefront destination in Chicago, offering a variety of activities and breathtaking views of Lake Michigan. My friends and I played volleyball here while catching rays.
Lincoln Park Zoo:
One of the oldest zoos in the country. It is also one of the few free zoos.
❄️ If you are in town for Christmas, visit the Lincoln Park Zoo for the ZooLights!
Oz Park:
If you are a Wizard Of Oz fan visit OZ PARK. You’ll see statues of Dorothy & Toto, the Tin Man, Scarecrow, and the Cowardly Lion. The park is dedicated to the author of The Wizard of Oz, Frank Baum who lived nearby. My girls had so much fun at this park.
Wrigley Field:
Sports enthusiasts shouldn't miss Wrigley Field, home to the Chicago Cubs. Immerse yourself in the rich baseball history of this iconic stadium, whether catching a game or taking a guided tour, it has captivated fans for more than 100 years. Click here to book a 90-minute tour of this majestic ballpark.
Must-Eat Chicago Foods:
Chicago Dog from Portillo’s:
A true Chicago Dog is a kosher, all-beef dog on a poppyseed bun topped with mustard, onions, relish, tomato slices, kosher pickle spear, sport peppers, and a dash of celery salt.
Deep-dish Pizza:
Lou Malnati’s Pizzeria is one of my favorites! Find a location near you.
Chicago Mix Popcorn:
Sweet-and-Salty combination of caramel popcorn and cheesy cheddar popcorn mixed. Don’t miss Garrett’s Popcorn, which opened in 1949. It’s so good! There is usually a line of others waiting to give it a try!
Chicago has the best food. Consider taking Chicago’s Favorite Foods Guided Walking Tour.
Fulton Market Kitchen: 311 N. Sangamon St. Chicago
Formerly an industrial zone, West Loop is a popular neighborhood known for its dining and nightlife. Once warehouses, most of the buildings are now home to some of Chicago’s top restaurants. Fulton Market is inspired by the 1980s NYC art scene and Wynwood Walls in Miami. This eclectic restaurant has different rooms with vintage furniture and a super cool vibe serving American, and Mediterranean food.
Chicago Pizza and Oven Grinder Company: 2121 N. Clark St. Chicago
This was my favorite restaurant when I lived in Chicago. I love their Mediterranean bread and salad. They are known for their pizza pot pies and grinders (sandwiches). This restaurant is small and very popular, you’ll need a reservation and they only take cash.
