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 Sights and River Cruise

Morning

Start your day with a classic breakfast at Lou Mitchell's, known for its delicious pancakes and old-school charm. After breakfast, take a leisurely walk to the Route 66 Sign to capture a nostalgic photo.

Afternoon

For lunch, head to Portillo's Hot Dogs and savor their famous Chicago-style hot dogs. Afterward, visit the iconic The Bean in Millennium Park and take in the unique reflections of the city skyline.

Evening

In the evening, enjoy a relaxing Chicago River 1.5-Hour Guided Architecture Cruise to learn about the city's stunning architecture. After the cruise, have a delightful dinner at The Purple Pig, known for its Mediterranean small plates. End the night with a touch of magic at the Chicago Magic Lounge, a hidden gem for a night of wonder and entertainment.

Bedtime

Find amazing hotels in Chicago, Illinois.

4.90
Route 66 Sign
Book Now

4.61
The Bean
Book Now

Skyline Views and Culinary Delights

Morning

Indulge in a delightful brunch at Lula Cafe, a local favorite for its farm-to-table dishes. Afterward, take a walk along the Chicago Riverwalk to enjoy the scenic views and vibrant atmosphere.

Afternoon

For a unique experience, visit the American Writers Museum, a hidden gem that celebrates the rich literary history of the United States. Afterward, have a late lunch at Xoco, a top spot for gourmet Mexican cuisine.

Evening

In the evening, soar to the top of the city at the 360 Chicago Observation Deck (Formerly John Hancock Observatory) and enjoy a drink with a view. Then, have a memorable dinner at Alinea, a three-Michelin-star restaurant known for its innovative and artistic dishes.

Bedtime

Find amazing hotels in Chicago, Illinois.