Chicago Itineraries
Explore Chicago: Attractions, Museums & Hidden Gems
Your personalized Chicago itinerary is just a click away. Choose from our expertly curated options below to start planning your perfect trip.

Gentle Chicago: Accessible 1-Day Autumn Itinerary for Seniors
Perfect for Seniors

Chicago in a Day — Friends' Energetic Summer Loop
Perfect for Friends

One Family Friendly Day in Chicago — Parks, Play & the Pier
Perfect for Families

Romantic 1-Day Chicago Escape — Autumn
Perfect for Couples

Kayaks, Cantilevers, and Terra-Cotta: Chicago’s Hands-On Modernism Safari
Perfect for Design Enthusiasts

Sketch + Paddle: Chicago Modernism from River to Rooftop
Perfect for Design Enthusiasts
Find the best things to do in Chicago
Plan your perfect Chicago trip with local itineraries and the best things to see and do. Whether you're looking for a day-trip or a week-long adventure, our unique travel guides have got you covered.
Top Chicago Attractions You Can't Miss
Iconic Sights to Hidden Gems
Escape Room Challenge at The Escape Game Chicago
90-minute immersive puzzle room built for groups — collaborate, race the clock, and celebrate wins together.
Modern Wing—Art Institute of Chicago: Modern & Material Studies
A concentrated look at 20th-century material experiments in architecture and design; situate local modernism within the museum’s curated context.
Guided architecture kayak — Urban Kayaks
A hands-on guided kayak on the Chicago River focusing on modernist and mid-century buildings — sketch while on shore stops and listen to commentary about facades, materials, and urban planning.
Art Institute of Chicago (Accessible galleries, seating, and coat check)
Spend a leisurely 2 hours inside: enjoy short visits to key galleries (Impressionists, American art). The museum offers wheelchairs, elevators, benches, and accessible restrooms.
Gentle stroll along the Chicago Riverwalk (flat, seated viewpoints)
Enjoy a short 30-minute, level stroll with frequent benches, public art, and calm views of downtown architecture without long distances.
Chicago River Architecture Cruise (accessible, seated guided experience)
A 75-minute guided architecture cruise highlighting iconic buildings with accessible boarding and seating—an excellent way to see Chicago without long walks.
Local Tips from the travel experts
Handpicked tips from top-rated activities in Chicago to help you make the most of your visit.
"The Rookery lobby is compact — practice capturing reflections and ornate metalwork with quick 10–15 minute gestures.Visit late afternoon for low-angle north light through the atrium; the contrast helps study material transitions.Security checks apply; if you want to linger to sketch, mention you’re a sketching designer — staff often allow short sketching sessions in the foyer."
Short visit to The Rookery lobby (Hoerr Schaudt restoration)
"Choose a café with good light and tables for spreading out reference images — use this time to mark buildings you still want to study.Export workshop photos and back up files; many cafés also have local art on the walls worth studying.If you're sourcing ceramics or textiles, jot down the studios you want to contact — Lillstreet often has referral lists."
Casual midday break & coffee (debrief and photo review)
"Plan to linger in the Impressionism galleries (Monet, Renoir) for soft, romantic scenes that pair well with quiet conversation.Ask for a map of quieter galleries on arrival to avoid crowded rooms and create intimate moments.Take advantage of the museum’s seating alcoves — ideal for a pause and a shared sketch or note."
Art Institute of Chicago — a focused visit
"Take measurements of installed vignettes to compare how pieces occupy space at full scale.Request material samples and inquire about lead times if you’re sourcing pieces for projects.Discuss with staff about local makers they collaborate with — DWR occasionally hosts pop-up maker events in the showroom."
Design Within Reach — showroom crawl
"Choose a room marked 'team-focused' or 'cooperative' — they’re optimized for groups of 4–6 and encourage shared problem-solving.If anyone is claustrophobic or has mobility limits, request accessibility notes beforehand; many rooms have alternate accommodations.Celebrate immediately after with a group photo in the lobby — staff will usually take one for you if asked."
Escape Room Challenge at The Escape Game Chicago
"Choose a table by the window to continue sketching interiors and note how material palettes affect mood.The Promontory often hosts local designers — ask staff if any nearby gallery openings are happening this week.If you’re carrying larger study pieces, ask for a quieter corner; the staff is used to design groups and can accommodate."
Lunch — The Promontory (Hyde Park)
"Stroller nap tip: the Lurie Garden has quieter corners with shade — lay a lightweight blanket in the stroller and let older babies/toddlers nap while you sit nearby.Changing and facilities: nearest family restrooms are at the Jay Pritzker Pavilion (a short stroll) if you need a changing table.Allergy tip: this green space can have blooms — if someone has pollen sensitivities, pick a bench on the paved edge for less direct exposure."
Quiet break / short nap at Lurie Garden (shaded benches)
"Book the guided architecture-level tour to access interior spaces and detailed commentary on material choices — essential for full compositional understanding.Try a 20-minute external sketch on the south lawn to capture the building’s horizontal sweep before entering for interior details.Photography restrictions apply indoors; bring a small notebook for quick interior notations and measured details."
Frank Lloyd Wright — Robie House guided tour
"Accessibility: The Cultural Center has elevators and accessible restrooms; staff can point you to quieter galleries with benches.Highlights: Don't miss the Preston Bradley Hall and the Tiffany Dome—there are many benches beneath the dome for comfortable viewing.Timing: This is a good pause to use the building's quiet spaces; if you tire, there's a small café nearby for a short refreshment."




