Chicago Itinerary by Locals for a perfect trip
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.
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.

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
Top Chicago Attractions You Can't Miss
Iconic Sights to Hidden Gems
A concentrated look at 20th-century material experiments in architecture and design; situate local modernism within the museum’s curated context.
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.
30-minute façade study of Louis Sullivan’s ornament and the thinness, scale, and emotive role of terra-cotta at street level.
Short visit to a landmark of reinforced-concrete modernism — observe material expression, light control, and spatial sequencing.
An open block to sit, edit, and annotate the morning’s sketches before dinner — recommended to process observations while fresh.
Core orientation to Chicago’s building typologies, model room, and rotating exhibitions that contextualize the day’s river route.
Local Tips from the travel experts
Handpicked tips from top-rated activities in Chicago to help you make the most of your visit.
"Prioritize galleries with architecture models and design objects (ask staff for the current Modern Wing highlights list).Use the museum benches to compare construction details in paintings/objects to nearby facades you saw from the river.Accessibility note: the Modern Wing is elevator-accessible and has tactile guides for select objects — request them at the information desk."
Modern Wing—Art Institute of Chicago: Modern & Material Studies
"Seats at the bar give a close-up of the open kitchen choreography and interior materials.Reserve early and request a table away from the main service aisle if you plan to unroll sketches.Discuss local ceramicists with staff — many restaurants source plates from Chicago studios and can share names."
Dinner at Avec — design-focused small-plates dining
"Book the timed-entry tour to guarantee access; guided tours focus on construction methods and original materials.Bring a measuring tape or use your phone’s measuring app for on-site proportion studies (where allowed).Note the landscape-house relationship — sit on the lawn edge (as allowed) to study composition and horizon lines."
Robie House (Frank Lloyd Wright) — Hyde Park tour
"Examine the storefront band at eye level — the tactile scale of the ornament reads differently than photos.Use a loupe or phone macro to study crazing and glaze textures; nearby benches are great for setting up magnification tools.If photographing, shoot late-afternoon for indirect light that reveals sculptural shadows on the reliefs."
Close Read: Sullivan Center (Carson, Pirie, Scott & Co.) — terra-cotta details
"Request a window table to continue sketching the park and skyline while you eat.Order something sharable to maximize table space for sketchbooks — locals like the house sausages and open-faced options.Ask staff about quieter corners if you want to spread out reference photos and samples for material studies."
Brunch and informal sketching session at The Gage
"Identify local brands and ask for business cards; many small makers show through Mart suites rather than storefronts.If you want hands-on time with materials, ask for a short demo — many reps will take 10–15 minutes for designers.Take photos of textures and joint details (many showrooms allow photos for designers) — they’re gold for later construction notes."
Design showroom browsing — The Merchandise Mart
"Check the gallery calendar before you go to target exhibits that emphasize material practice or process-based work.Ask gallery staff about local designers in the exhibit and whether artist talks or studio visits are scheduled.Use your visit to gather gallery contact info for future studio visits or collaborations."
Gallery visit: The Arts Club of Chicago or rotating downtown design galleries
"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
"Find a bench facing the river to lay out spreads and compare studies; grouping studies by façade helps later analysis.If you want critique, DM a local organizer (Chicago Urban Sketchers) — many designers meet here in afternoons.If any pages got damp, pin them under a heavy object in your daypack to flatten and dry before evening."
Break & editing time — rest and refine sketches

