10-day Chicago itinerary

A ready-made 10-day sightseeing plan for Chicago — top-rated attractions, one morning-to-evening schedule per day. Use it as-is or as a starting point; every stop links to full details, hours, and fees. Hungry? Pick your own spot to eat — we don't bake that decision into the plan for you.

1Day 1

  1. 9:00 AM
    2–4 hr stay
    Chicago Architecture River Cruise5.0

    112 E. Wacker Drive, chicago

    Experience Chicago's iconic skyline and rich history from the water

  2. 1:30 PM
    1–2 hr stay
    Art Institute of Chicago4.8

    111 South Michigan Avenue, chicago

    Discover world famous art masterpieces in the heart of downtown Chicago

  3. 4:15 PM
    2–4 hr stay
    Garfield Park Conservatory4.8

    300 N Central Park Ave, chicago

    Landscape art under glass

2Day 2

  1. 9:00 AM
    2–4 hr stay
    Music Box Theatre4.8

    3733 N Southport Ave, chicago

    Chicago's premier venue for independent, foreign, and classic cinema since 1929.

  2. 1:30 PM
    1–2 hr stay
    Shakespeare Theatre4.8

    800 E Grand Ave, chicago

    Acclaimed theater venue showcasing classic and contemporary plays on Navy Pier

  3. 4:15 PM
    2–4 hr stay
    The 6064.8

    1805 N Ridgeway Ave, chicago

    An elevated park connecting historic Chicago neighborhoods for walkers and cyclists

3Day 3

  1. 9:00 AM
    2–4 hr stay
    Wrigley Field4.8

    1060 W Addison St, chicago

    Historic home of the Chicago Cubs featuring iconic baseball game experiences

  2. 1:30 PM
    1–2 hr stay
    Buckingham Fountain4.7

    301 S. Columbus Dr., chicago

    Chicago's iconic landmark fountain offering majestic water and light shows

  3. 4:15 PM
    2–4 hr stay
    Chicago Cultural Center4.7

    78 E Washington St, chicago

    Explore free visual art exhibitions inside a stunning historic landmark.

4Day 4

  1. 9:00 AM
    2–4 hr stay
    Grant Park4.7

    331 E Randolph St, chicago

    Chicago's iconic waterfront green space packed with cultural landmarks and gardens

  2. 1:30 PM
    1–2 hr stay
    Lincoln Park4.7

    N Lincoln Ave & W Fullerton Pkwy, chicago

    Nature lovers dream

  3. 4:15 PM
    2–4 hr stay
    Maggie Daley Park4.7

    337 E Randolph St, chicago

    A scenic downtown Chicago destination offering outdoor recreation for all ages

5Day 5

  1. 9:00 AM
    2–4 hr stay
    Millennium Park & Cloud Gate4.7

    201 East Randolph Street, chicago

    Chicago's premier civic park featuring iconic public art and vibrant spaces

  2. 1:30 PM
    1–2 hr stay
    Museum of Science and Industry4.7

    5700 S DuSable Lake Shore Dr., chicago

    Explore hands on science and industry exhibits at Chicago's premier interactive museum

  3. 4:15 PM
    2–4 hr stay
    Thalia Hall4.7

    1807 S. Allport St., chicago

    Historic 1892 Pilsen concert venue hosting live music and performances

6Day 6

  1. 9:00 AM
    2–4 hr stay
    The Chicago Theatre4.7

    175 N State St, chicago

    An iconic landmark hosting live music and comedy in downtown Chicago

  2. 1:30 PM
    1–2 hr stay
    The Field Museum4.7

    1400 S DuSable Lake Shore Dr., chicago

    Discover natural history treasures, ancient mummies, and iconic dinosaur fossils.

  3. 4:15 PM
    2–4 hr stay
    The Peggy Notebaert Nature Museum4.7

    2430 N Cannon Dr, chicago

    Explore urban nature and vibrant butterflies in Chicago's Lincoln Park

7Day 7

  1. 9:00 AM
    2–4 hr stay
    Chicago History Museum4.6

    1601 N Clark St, chicago

    Explore the rich stories, artifacts, and culture of the Windy City

  2. 1:30 PM
    1–2 hr stay
    Lincoln Park Zoo4.6

    2001 North Clark Street, chicago

    Historic free admission zoo in Chicago featuring diverse global wildlife

  3. 4:15 PM
    2–4 hr stay
    Navy Pier4.6

    600 E Grand Ave, chicago

    An iconic lakeside destination with amusement rides, dining, and scenic views.

8Day 8

  1. 9:00 AM
    2–4 hr stay
    North Ave Beach4.6

    1600 N Lake Shore Dr., chicago

    Chicago's energetic lakefront beach featuring sandy shores and skyline views

  2. 1:30 PM
    1–2 hr stay
    Shedd Aquarium4.6

    1200 S DuSable Lake Shore Dr., chicago

    Explore world class marine habitats at Chicago's famous Shedd Aquarium.

  3. 4:15 PM
    2–4 hr stay
    The Second City4.6

    230 W North Ave, chicago

    Discover Chicago's premier improv and sketch comedy stage in Old Town

9Day 9

  1. 9:00 AM
    2–4 hr stay
    Wicker Park4.6

    N Damen Ave & N Milwaukee Ave, chicago

    A vibrant community green space featuring gardens, events, and sports fields

  2. 1:30 PM
    1–2 hr stay
    John Hancock Building & 360 Chicago4.5

    875 N Michigan Ave, chicago

    Soar above Michigan Avenue for breathtaking Chicago skyline and lakefront views

  3. 4:15 PM
    2–4 hr stay
    Starbucks Reserve Chicago Roastery4.5

    646 N Michigan Ave, chicago

    Explore five floors of artisanal coffee, craft cocktails, and fresh pastries.

10Day 10

  1. 9:00 AM
    2–4 hr stay
    Willis Tower Skydeck4.5

    233 S Wacker Dr, chicago

    Experience breathtaking panoramic views high above Chicago from Willis Tower Skydeck

  2. 1:30 PM
    1–2 hr stay
    Green Mill Jazz Club4.4

    4802 N Broadway St, chicago

    Experience authentic live music at Chicago's historic Prohibition-era jazz lounge

  3. 4:15 PM
    2–4 hr stay
    Museum of Contemporary Art4.4

    220 E Chicago Ave, chicago

    Explore innovative contemporary art and dynamic exhibitions in downtown Chicago

Want more options? Browse things to do in Chicago, places to eat, or the full Chicago vacation guide.