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.

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

Gentle Chicago: Accessible 1-Day Autumn Itinerary for Seniors

Perfect for Seniors

1 Day
Chicago in a Day — Friends' Energetic Summer Loop
Chicago in a Day — Friends' Energetic Summer Loop

Chicago in a Day — Friends' Energetic Summer Loop

Perfect for Friends

1 Day
One Family Friendly Day in Chicago — Parks, Play & the Pier
One Family Friendly Day in Chicago — Parks, Play & the Pier

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

Perfect for Families

1 Day
Romantic 1-Day Chicago Escape — Autumn
Romantic 1-Day Chicago Escape — Autumn

Romantic 1-Day Chicago Escape — Autumn

Perfect for Couples

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

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

Perfect for Seniors

2 Days
Chicago in 48 Hours — Friends' Fun & Vibrant Weekend
Chicago in 48 Hours — Friends' Fun & Vibrant Weekend

Chicago in 48 Hours — Friends' Fun & Vibrant Weekend

Perfect for Friends

2 Days
2-Day Family-Friendly Summer Visit to Chicago
2-Day Family-Friendly Summer Visit to Chicago

2-Day Family-Friendly Summer Visit to Chicago

Perfect for Families

2 Days
Romantic 2‑Day Couples Getaway in Chicago — Autumn
Romantic 2‑Day Couples Getaway in Chicago — Autumn

Romantic 2‑Day Couples Getaway in Chicago — Autumn

Perfect for Couples

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

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

Perfect for Seniors

3 Days
3-Day Fun & Vibrant Friends' Weekend in Chicago
3-Day Fun & Vibrant Friends' Weekend in Chicago

3-Day Fun & Vibrant Friends' Weekend in Chicago

Perfect for Friends

3 Days
Family-friendly 3-day Chicago Summer Itinerary
Family-friendly 3-day Chicago Summer Itinerary

Family-friendly 3-day Chicago Summer Itinerary

Perfect for Families

3 Days
Romantic 3-Day Chicago Getaway for Couples (Autumn)
Romantic 3-Day Chicago Getaway for Couples (Autumn)

Romantic 3-Day Chicago Getaway for Couples (Autumn)

Perfect for Couples

3 Days
Kayaks, Cantilevers, and Terra-Cotta: Chicago’s Hands-On Modernism Safari
Kayaks, Cantilevers, and Terra-Cotta: Chicago’s Hands-On Modernism Safari

Kayaks, Cantilevers, and Terra-Cotta: Chicago’s Hands-On Modernism Safari

Perfect for Design Enthusiasts

3 Days
Sketch + Paddle: Chicago Modernism from River to Rooftop
Sketch + Paddle: Chicago Modernism from River to Rooftop

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.

See Chicago things to do
Itinerary image 1
Itinerary image 2
Itinerary image 3
Itinerary image 4
Itinerary image 5

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

"Buy timed-entry tickets in advance for a quieter experience; weekdays and early afternoons are less crowded in June.Stroller parking is available near the entrance; bring a small backpack with snacks and wipes for quick changes.Look for the dedicated toddler spaces and quieter activity corners if younger kids need a low-stimulus spot."

Chicago Children's Museum at Navy Pier (hands-on exhibits)

"Reserve an indoor seat on the lower deck to avoid wind and have easier access to restrooms.Notify staff when booking if you need wheelchair assistance boarding; many companies provide staff help.Bring layered clothing — the river can be cooler; September afternoons are pleasant but a light sweater helps."

Chicago Architecture River Cruise (narrated, mostly seated, indoor options)

"Recommended ages: 1–8; plan 1.5–2.5 hours with a quiet corner break for infants and toddlers who may need a nap.Accessibility: family restrooms and nursing rooms are available — ask staff for the nearest changing table and quieter spaces if someone needs a calm area.Buy timed-entry tickets online to shorten queues, and bring socks for kids as some play areas require them."

Chicago Children's Museum (Navy Pier) — hands-on play for young kids

"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)

"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

"Split-up and order from different counters (pizza, pasta, seafood) then reconvene at one big table to sample everything.Reserve a table or arrive slightly off-peak (after 13:00) if your group prefers a seated meal rather than counter grazing.Take turns picking items to keep costs balanced; Eataly’s deli items pack well for a casual lakeside snack later."

Lunch & grazing at Eataly Chicago (River North)

"The building has elevators and accessible restrooms; staff can point out the shortest route between highlights.Take a guided mini-tour if available — these are usually short and seated-friendly.Sit in the central stair hall (there are bench areas) to admire the domes without climbing stairs."

Chicago Cultural Center — calm galleries and accessible architecture

"If you want the wheel, buy skip-the-line tickets online and meet at the wheel entrance to avoid long queues.Navy Pier has many photo spots; pick one person as the 'photographer' to keep photos consistent and fun.If someone prefers to skip rides, plenty of seating and people-watching opportunities make waiting enjoyable for the group."

Navy Pier & Centennial Wheel (optional quick visit)