AI Travel Planner

AI Travel PlannerRoam AroundAI Travel Planner


Starting date
day 1
December 6
Morning. Start your day off with a delicious breakfast at The Original Pancake House, where you can indulge in their famous Dutch Baby and fluffy pancakes. After breakfast, head over to the Chicago Riverwalk to enjoy the scenic views of the city while strolling along the waterfront.
Afternoon. Make your way to the iconic Magnificent Mile, where you can shop until you drop at high-end retailers like Neiman Marcus, Gucci, and Louis Vuitton. Take a break from shopping and visit the Museum of Contemporary Art, where you can admire works of art from both established and emerging artists.
Evening. For dinner, head to RPM Italian, where you can savor modern Italian cuisine in an elegant setting. After dinner, catch a show at the historic Chicago Theatre, which has hosted legendary performances since 1921.
Bedtime. Find amazing hotels in
day 2
December 7
Morning. Visit the Art Institute of Chicago, one of the oldest and largest art museums in the country, where you can marvel at works by artists like Monet, Picasso, and Van Gogh. Grab lunch at the nearby Lou Malnati's Pizzeria for a taste of the city's famous deep-dish pizza.
Afternoon. Take a stroll through Millennium Park, home to the iconic Cloud Gate sculpture (also known as the Bean) and the stunning Jay Pritzker Pavilion. Stop by the nearby Chicago Cultural Center to see the Tiffany glass dome and other beautiful art and architecture.
Evening. For dinner, head to The Signature Room at the 95th for breathtaking views of the city and delicious American cuisine. End your night with a cocktail at The Violet Hour, an award-winning speakeasy with a sophisticated atmosphere.
Bedtime. Find amazing hotels in
day 3
December 8
Morning. Get your adrenaline pumping with a thrilling speedboat ride on Lake Michigan with Seadog Cruises. After the ride, head over to Navy Pier to explore the shops, restaurants, and attractions like the Chicago Children's Museum and the Centennial Wheel.
Afternoon. Visit the historic Water Tower, one of the few buildings to survive the Great Chicago Fire of 1871, and browse through the luxury boutiques on the nearby Oak Street. Stop by Garrett Popcorn Shops for a bag of the city's famous Garrett Mix popcorn.
Evening. For dinner, head to The Purple Pig, a popular spot for Mediterranean-inspired small plates and a vast selection of wines. Afterward, catch a comedy show at The Second City, where famous comedians like Tina Fey and Stephen Colbert got their start.
Bedtime. Find amazing hotels in
day 4
December 9
Morning. Visit the Lincoln Park Zoo, a free zoo with over 1,000 animals from around the world. Grab brunch at the nearby Cafe Ba-Ba-Reeba!, a Spanish tapas restaurant with a lively atmosphere.
Afternoon. Take a walk through the beautiful Lincoln Park Conservatory, where you can see a variety of exotic plants and flowers. Then head to the nearby Second City neighborhood to explore the quirky shops and vintage boutiques.
Evening. For dinner, head to The Gage, a gastropub with a cozy atmosphere and a menu of classic American fare. End your night with a cocktail at the speakeasy-style The Office, located in the back of The Aviary bar.
Bedtime. Find amazing hotels in
day 5
December 10
Morning. Start your day with a visit to the Chicago History Museum, where you can learn about the city's rich history and culture. Afterward, grab a quick bite at Portillo's, a Chicago classic known for its hot dogs and Italian beef sandwiches.
Afternoon. Head to the John Hancock Center, where you can take a thrilling ride up to the 360 Chicago Observation Deck for breathtaking views of the city. Then, visit the Museum of Broadcast Communications to see exhibits on the history of radio and television.
Evening. For dinner, head to RPM Steak, where you can enjoy delicious steaks and seafood in a sleek and modern setting. End your night with a drink at The Berkshire Room, a cozy cocktail lounge with a vintage-inspired atmosphere.
Bedtime. Find amazing hotels in
Rate This Itinerary
Share trip