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

Gentle 2-Day Chicago Visit for Seniors (Accessible, Relaxed Pace)
Perfect for Seniors

Chicago in 48 Hours — Friends' Fun & Vibrant Weekend
Perfect for Friends

2-Day Family-Friendly Summer Visit to Chicago
Perfect for Families

Romantic 2‑Day Couples Getaway in Chicago — Autumn
Perfect for Couples

Gentle 3-Day Chicago Tour for Seniors — Comfortable, Accessible, and Scenic
Perfect for Seniors

3-Day Fun & Vibrant Friends' Weekend in Chicago
Perfect for Friends

Family-friendly 3-day Chicago Summer Itinerary
Perfect for Families

Romantic 3-Day Chicago Getaway for Couples (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
The Escape Game Chicago — 60–90 minute room (team challenge)
A playful puzzle experience where your group works together to escape — great for bonding and friendly competition.
Kayak the Chicago River — Urban Kayaks (guided or rental)
Paddle the river for a playful, active view of Chicago's architecture — a small-group-friendly activity in spring weather.
Stroll along the Chicago Riverwalk (easy, stroller-friendly)
A pretty, paved riverside route with benches, public art and occasional snack carts — short and relaxing before dinner.
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.
Millennium Park: easy-access outdoor stroll and Cloud Gate (the 'Bean')
Gentle, mostly step-free paths, benches and shaded spots. A good short introduction to Chicago with minimal walking.
Art Institute of Chicago — accessible galleries and short guided route
World-class collection with elevators, wheelchairs available at coat check, and plenty of seating. Focus on highlights to keep the visit comfortable.
Local Tips from the travel experts
Handpicked tips from top-rated activities in Chicago to help you make the most of your visit.
"Accessibility: The building has step-free entry, elevators, and plentiful seating in the main halls — great for a rest in air-conditioned comfort.Insider: Ask staff about quieter galleries or current daytime talks (often free) so you can sit and listen rather than stand for long periods.Facilities: Public restrooms (including accessible stalls) are on the lower floors; take a short restroom break here before lunch to reduce walking later."
Chicago Cultural Center — landmark interiors and quiet galleries
"Pre-book to guarantee seats together; ask for lower-deck seating if anyone in the group prefers shade or calmer views.Bring a lightweight jacket — breezes on the river can be cool in May, especially later in the evening.Use the cruise as a relaxed photo/opportunity to plan dinner — split tickets or pay one person and settle up with apps after."
Architecture River Cruise — Shoreline Sightseeing
"Stick to a short stretch (e.g., Oak Street to the Water Tower) to avoid long walks.Use department stores (indoor, elevator-equipped) as rest stops and for accessible restroom access.Sit frequently — many sidewalks have benches; consider a short coffee pause between stores."
Gentle window-shopping on the Magnificent Mile (short distances and benches)
"Pick a shorter planetarium show for young attention spans; many are 20–30 minutes and very engaging for ages 4+.The outdoor area has paved paths and stroller access with photo spots that parents love — ideal for family shots.There are elevators throughout; staff can point you to quieter galleries for toddlers who may be sensitive to loud audio."
Visit Adler Planetarium (short, playful exhibits and skyline views)
"Popular with families — request a high chair and ask servers about smaller portion or split-plate options for picky eaters.There may be a short wait; put a stroller to the side and grab a table near the door for quick exits if a child needs a nap.Menu customizations are common — ask about dairy or gluten swaps if anyone has allergies."
Lunch at Wildberry Pancakes and Cafe (near Millennium Park)
"Best times for photos and less crowding are mid-morning (after 9:30) on weekdays in June.There are public restrooms nearby (northwest side of the park) and shady benches along the Lurie Garden edge for snack breaks.For toddlers, bring a quick-change towel — kids often want to splash at Crown Fountain."
Millennium Park – Cloud Gate (the 'Bean') and Crown Fountain
"Arrive for opening or mid-morning to catch keeper talks and avoid the midday crowd; paths are paved and stroller-friendly.There are multiple family restrooms with changing tables near the main entrance and in the Farm-in-the-Zoo area.Bring a small cooler or snacks — picnic tables are nearby and save time if waiting for tired kids."
Lincoln Park Zoo (free, stroller-friendly loop)
"Lou Mitchell's is popular: if the group is big, split into two nearby tables and sync orders to stay together.Classic pre-1930s decor makes for fun vintage photos — perfect for friends who want a lively, nostalgic vibe.Ask servers about daily specials and the 'to-go' donut treat they often hand out if you want a small dessert to share later."
Brunch at Lou Mitchell's (classic Chicago diner)
"Reserve wheelchair use at the coat check on arrival and plan a short list of must-see exhibits to keep standing minimal.Use the museum café for a seated lunch or frequent rest stops; restrooms and elevators are clearly marked.Avoid peak exhibit shows that require standing—ask staff about timed demonstrations with seating."




