Sketch + Paddle: Chicago Modernism from River to Rooftop
A crisp, design-forward 3-day itinerary for enthusiasts who want to sketch modernist architecture, meet makers, and paddle the Chicago River — blending museum visits, studio stops, hands-on workshops, and rooftop vantage points.
Highlights
- Guided architecture kayak on the Chicago River
- Deep dives at the Chicago Architecture Center and Art Institute’s modern design holdings
- Studio and gallery visits in River North
- Sketch sessions at S.R. Crown Hall and Robie House
- Rooftop sketching with panoramic views at Cindy’s
Itinerary
Day 1
River-focused day: warm up with espresso, paddle the Chicago River to study facades from water level, then ground those observations at the Chicago Architecture Center and nearby modernist interiors.
Pre-departure sketch warm-up & coffee — Sawada Coffee
A quick, design-minded caffeine stop to loosen the hand and review maps of the river façades you'll study. Compact, strong espresso and plenty of counter space for sketch pads.
Local tips:
- Bring a small sketchbook (A5) — the narrow front counter is best for quick 10–15 minute gestures.
- If mobility is a concern, ask for a seat near the door to avoid the step up; the staff know frequent sketchers.
- Turn your sketchbook vertically to capture the tall riverfront buildings visible from the window; note the rhythm of windows and piers for later annotation.
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.
Local tips:
- Wear quick-dry clothing and bring a waterproof sleeve for sketchbooks; the guide will suggest short shore stops ideal for quick studies.
- Ask guides for pointers on sightlines to sketch the three most legible façades (they often know which buildings sit low enough for unobstructed views).
- For accessibility, Urban Kayaks provides stable sit-on-top kayaks and a shore crew to help launches — request assistance when booking.
Quick change & transfer
A brief shore return, rinse off, and walk to the Riverwalk for lunch — time to transfer gear and consolidate sketches.
Local tips:
- Use this time to photograph references of façades you sketched; photos help refine ink lines later.
- If you have wet gear, towel off and sit in the sun along the Riverwalk rail to speed drying.
- Keep valuables in a waterproof bag during the paddle and move them now to a dry daypack for the museum visit.
Riverside lunch — River Roast (Riverwalk)
A roast-and-grill spot on the Riverwalk with large windows and table space for unfolding sketches — ideal for annotating notes from the paddle.
Local tips:
- Request a window table to re-check sightlines from this morning’s paddle; the terrace light is best for tonal studies mid-day.
- For pace, order a share plate so you can continue discussing compositional choices while you eat.
- If you prefer quieter sketching, the upstairs seating is calmer and often used by local designers for working lunches.
Transfer to Chicago Architecture Center
Walk along the river to the museum hub — short transit to reorganize sketches and check the center’s exhibit and seminar schedules.
Local tips:
- Stop at the river viewpoints on the way for additional reference shots — the CAC staff recommend particular façades for study.
- If you need restroom or changing space, the Architecture Center has facilities and coat storage for small bags.
- Buy an exhibition guide on arrival to locate highlights focusing on modernist Chicago architects.
Chicago Architecture Center — exhibitions + sketch lab
Focused time exploring exhibitions about Chicago modernism and joining the center’s sketch lab or quick workshop (check day’s offerings) — ideal for measured studies of plans and elevations.
Local tips:
- Head straight to the scale-model gallery to practice drawing massing relationships — models are great for quick proportion studies.
- Ask the desk about drop-in sketch labs; they sometimes offer instructor feedback geared to urban sketching techniques.
- Accessibility note: the center is fully accessible; ask for an audio-descriptive tour if you want a verbal walkthrough of material detailing.
Short visit to The Rookery lobby (Hoerr Schaudt restoration)
A study stop to see Burnham & Root’s landmark lobby with Frank Lloyd Wright’s later interior touches — compelling for texture and light studies.
Local tips:
- 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.
Break & editing time — rest and refine sketches
An open block to sit, edit, and annotate the morning’s sketches before dinner — recommended to process observations while fresh.
Local tips:
- 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.
Dinner — avec
An intimate, design-conscious small-plates restaurant favored by locals — a calm, cultivated dinner to review day-one studies.
Local tips:
- Ask for a corner table with good overhead light for continuing to annotate sketches between courses.
- The open-plan kitchen and simple, modern plating make a good subject for composition sketching if you want to practice still-life between architectural sessions.
- If dining with designers, request the wine-pairing tasting for a paced meal that leaves time for post-dinner talk.
Day 2
Museum and studio day: modern design collections in the morning, showroom and gallery visits in the afternoon, an afternoon workshop at SAIC, and rooftop sketching at dusk.
Art Institute of Chicago — focused study on modern design
Concentrate on the modern and decorative arts holdings: furniture, industrial design, and graphic systems — practice measured studies of form and material.
Local tips:
- Use the museum map to locate the modern design and architecture galleries; spend most time on furniture and industrial design cases.
- Bring pencils for tonal studies (graphite works better than ink in crowded galleries); stools are available in some rooms for longer studies.
- Accessibility note: the institute is fully accessible; request a quieter entrance time for less foot traffic if you need still-space to draw.
Transfer to Merchandise Mart (showroom block)
Short transit to The Merchandise Mart to browse design showrooms — a concentrated place to see local manufacturers and material samples.
Local tips:
- Check showroom hours in advance and email any manufacturers you want to meet; many require appointment for trade access.
- Collect material swatches and catalogs for tactile references; showroom reps often hand out small sample cards.
- The building is large — pick two floors (furniture and lighting) to avoid overwhelm; bring a rolling bag for samples.
Design showroom browsing — The Merchandise Mart
Visit curated showrooms for furniture, lighting, and textiles — great for connecting modernist vocabulary to contemporary production.
Local tips:
- 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.
Lunch — Ema (River North)
A bright, modern Mediterranean spot with clean plating and plenty of table space for mid-day sketch editing and conversation.
Local tips:
- Order a spread of mezzes to sketch compositional negative spaces — the plating is very photographic.
- Window seating offers great light for color studies on your portable palette or colored pencils.
- If you’re meeting a local designer, Ema’s layout supports small-group conversation without shouting — reserve a table.
River North gallery walk — Monique Meloche Gallery
A short, focused gallery stop to see contemporary works by Chicago-based artists and designers — useful to connect modernist lineage to current practice.
Local tips:
- Find works that play with materiality — many local artists reinterpret industrial surfaces; sketch material experiments.
- Gallery staff are often happy to introduce visiting curators or local makers — mention you’re a visiting designer to start a conversation.
- Light in the gallery is controlled; bring a small folding lamp only if staff permits longer close-study time.
River North gallery stop — Kavi Gupta Gallery
A complementary gallery visit showcasing large-scale and material-forward work by regional contemporary artists — excellent for studying scale and negative space.
Local tips:
- Practice thumbnail sketches of scale relationships to large installations; note how human figures are used for proportion cues.
- If a show references industrial techniques, ask the gallery director about local fabricators and workshops.
- Many galleries have printed exhibition essays — grab a copy for typographic and layout inspiration for your own presentation boards.
Workshop / continuing studies session — School of the Art Institute of Chicago (SAIC)
An evening sketching or print-focused workshop through SAIC Continuing Studies (pre-book) — hands-on instruction with materials and critique.
Local tips:
- Pre-book the SAIC workshop — seats fill quickly; request a materials list and bring your preferred pens for continuity.
- Workshop spaces often have easels and larger tables—this is a great time to switch from pocket sketches to study pieces.
- Accessibility note: SAIC studios are equipped with adjustable-height tables; request accommodations when registering.
Rooftop sketch session & evening views — Cindy's Rooftop (Chicago Athletic Association)
A rooftop terrace with panoramic views over Millennium Park and Lake Michigan — a design-appropriate vantage to translate city rhythms to compositional thumbnails at dusk.
Local tips:
- Arrive 30 minutes before sunset for the best shifting light — sketch large shapes first, then add detail as lights come on.
- The rooftop has pergolas and benches that frame views; use them to practice cropping and framing choices.
- Seating can fill up — reserve a table and ask for a corner spot with an unobstructed sightline to the park and skyline.
Day 3
Modernist institution day: Mies’s S.R. Crown Hall, Frank Lloyd Wright’s Robie House, neighborhood exploration in Hyde Park, and a final reflective sketch walk along the Riverwalk.
S.R. Crown Hall — sketch study of Mies van der Rohe’s space (IIT)
A concentrated sketching session in Mies’ S.R. Crown Hall — study proportion, structure, and the interplay of light and steel.
Local tips:
- Get permission at the front desk for a quiet corner to set up a small drawing board; longer sketch sessions are often allowed for students and designers.
- Use a ruler or straightedge for studying the orthogonal grids — practicing measured perspective here pays dividends later.
- Accessibility note: the building is accessible; ask staff if any temporary exhibits restrict movement before arriving.
Transfer to Robie House (Hyde Park)
Short rail or rideshare transfer south to Hyde Park — use transit time to review floor plans and compositional ideas for Wright’s horizontality.
Local tips:
- If using public transit, take the Metra/CTA and sit on the left side of the train for the best approach views into Hyde Park.
- Use transfer time to annotate proportions from photos taken earlier of Mies’ facade to compare approaches.
- If you prefer a scenic route, request a rideshare along Lake Shore Drive for extra shoreline references.
Frank Lloyd Wright — Robie House guided tour
Guided visit of Robie House to study Wright’s planar compositions, low-slung horizontality, and integration of ornament and plan.
Local tips:
- 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.
Lunch — The Promontory (Hyde Park)
A neighborhood spot with thoughtful interiors and good light — a chance to reflect on Wright’s proportions and edit morning sketches.
Local tips:
- 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.
Transfer to Chicago Cultural Center
Return toward downtown to visit the Cultural Center’s rotunda, decorative ceilings, and rotating design exhibitions.
Local tips:
- Plan for a 45–60 minute transfer by transit; use the trip to sort sketches into themes (material, proportion, ornament).
- If carrying larger boards, consider a light backpack and request a short luggage-hold at the Center’s information desk.
- Check the Cultural Center’s calendar in advance; rotating exhibits often include design installations or local craft shows.
Chicago Cultural Center — mosaics, rotunda, and small design exhibits
A compact study of decorative arts and civic-scale ornamentation — great for pattern studies and typographic references.
Local tips:
- The Tiffany dome and mosaics are prime subjects for pattern thumbnails — practice translating ornament into modular sketches.
- Ask at the information desk about current design- or craft-focused exhibits and any curator talks scheduled that day.
- Accessibility note: the building is fully accessible; elevators connect major exhibition spaces for those with mobility needs.
Final sketch walk along the Chicago Riverwalk — wrap-up session
An unstructured, reflective sketching walk along the Riverwalk to synthesize three days of observations — pick a final composition to develop into a study.
Local tips:
- Pick a single compositional challenge (e.g., rhythm of windows, reflection studies, or human scale) and restrict your palette to 2–3 elements.
- If you want feedback, schedule a quick midday check-in with a local designer or a member of Chicago Urban Sketchers (many meetup publicly on the Riverwalk).
- Bring a folding stool or use low river-edge ledges for comfortable longer studies; be mindful of pedestrian flow and keep gear compact.