New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Chicago Weekend Getaway with Mom Itinerary

Last updated: 2024 Jun 14

Iconic Chicago Sights and River Cruise

Morning

Start your day with a classic breakfast at Lou Mitchell's, a historic diner in Chicago known for its delicious meals. After breakfast, take a leisurely walk to the Route 66 Sign to capture a piece of American history.

Afternoon

Head to The Bean, officially known as Cloud Gate, in Millennium Park. Enjoy taking photos and admiring the unique sculpture. For lunch, savor the famous deep-dish pizza at Lou Malnati's Pizzeria.

Evening

Visit the iconic Navy Pier and take a spin on the Centennial Wheel with the Regular & Express Ticket. Afterward, enjoy a relaxing Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's stunning architecture. For dinner, experience the historic Green Mill, a legendary jazz club with a great atmosphere.

Bedtime

Find amazing hotels in Chicago, Illinois.

Magic and Comedy in the Windy City

Morning

Enjoy a leisurely morning before heading to The Purple Pig for a delightful brunch experience.

Afternoon

Explore the vibrant neighborhood of Wicker Park and have a late lunch at Big Star, known for its tacos and outdoor patio.

Evening

Immerse yourself in the world of magic at the Chicago Magic Lounge, a unique and entertaining experience. Conclude your trip with a visit to the world-renowned The Second City Comedy Club, where many comedy legends have performed.

Bedtime

Find amazing hotels in Chicago, Illinois.