Chicago itinerary

1. 1

   Chicago Marathon - Sunday 11 October 2026

   The Bank of America Chicago Marathon runs on Sunday 11 October 2026, the 48th running, and it is one of the World Marathon Majors. Over 200,000 people applied for the 2026 race, a record, with around 53,000 expected to…

   Address

   Grant Park, 337 E Randolph St, Chicago, IL 60601

   Nearest transit

   Millennium Station (Metra Electric) or Monroe (Red Line), 5-min walk

2. 2

   The Morton Arboretum - 1,700 Acres of Peak Colour

   The Morton Arboretum is 1,700 acres of trees in Lisle, 25 miles west of downtown, founded in 1922 by Joy Morton of the salt company. It holds more than 4,000 kinds of trees and plants from around the world, laid out…

   Address

   4100 IL-53, Lisle, IL 60532

   Nearest transit

   Lisle station (Metra BNSF), then a short rideshare

3. 3

   The Lakefront Trail - Eighteen Miles Beside the Water

   The Lakefront Trail runs 18.5 miles along Lake Michigan from Ardmore Avenue in the north to 71st Street in the south, entirely on public land, because Chicago's 19th-century planners kept the shoreline out of private…

   Address

   Oak Street Beach, 1000 N Lake Shore Dr, Chicago, IL 60611

   Nearest transit

   Chicago station (Red Line), 10-min walk to Oak Street Beach

4. 4

   The Architecture River Cruise - Best in Clear October Air

   The Chicago Architecture Center river cruise is the one tour in the city that nearly everyone agrees is worth the money. It runs 90 minutes along all three branches of the Chicago River with a trained volunteer docent…

   Address

   Chicago Architecture Center, 111 E Wacker Dr, Chicago, IL 60601

   Nearest transit

   State/Lake or Lake station (Loop 'L' lines), 4-min walk

5. 5

   Millennium Park and the Lurie Garden - Grasses at Their Peak

   Millennium Park opened in 2004, four years late and massively over budget, on top of what had been a railway yard, and it is now the most visited attraction in the Midwest. Cloud Gate, the polished steel sculpture…

   Address

   201 E Randolph St, Chicago, IL 60602

   Nearest transit

   Washington/Wabash station (Loop 'L'), 3-min walk

6. 6

   Garfield Park Conservatory - Free, Warm and Under Glass

   Garfield Park Conservatory is among the largest conservatories in the United States, built between 1906 and 1908 to a design by Jens Jensen that treated the glasshouse itself as landscape art rather than a greenhouse…

   Address

   300 N Central Park Ave, Chicago, IL 60624

   Nearest transit

   Conservatory-Central Park Drive station (Green Line), at the entrance

7. 7

   The Alfred Caldwell Lily Pool - Three Acres Nobody Finds

   The Alfred Caldwell Lily Pool is a small hidden landscape inside Lincoln Park, designed in the 1930s in the Prairie School style to imitate a river cut through limestone, with a stone council ring, a waterfall and a…

   Address

   125 W Fullerton Pkwy, Chicago, IL 60614

   Nearest transit

   Fullerton station (Red, Brown and Purple Lines), 12-min walk

8. 8

   The Art Institute of Chicago - Navigable Again in October

   The Art Institute of Chicago holds one of the great Impressionist and Post-Impressionist collections outside France, including Seurat's A Sunday on La Grande Jatte, which fills most of a wall, and more Monet than almost…

   Address

   111 S Michigan Ave, Chicago, IL 60603

   Nearest transit

   Adams/Wabash station (Loop 'L'), 3-min walk

9. 9

   Skydeck at Willis Tower - Four States on a Clear Day

   Skydeck occupies the 103rd floor of the Willis Tower, 1,353 feet up, and was the tallest building in the world for 25 years after it opened as the Sears Tower in 1973. The Ledge is the reason people come: glass boxes…

   Address

   233 S Wacker Dr, Chicago, IL 60606

   Nearest transit

   Quincy station (Loop 'L') or LaSalle (Blue Line), 5-min walk

10. 10

    Jackson Park and the Osaka Garden - The Last Colour to Turn

    Jackson Park was laid out by Frederick Law Olmsted and hosted the 1893 World's Columbian Exposition, the fair that gave Chicago the nickname the White City and left behind the building now housing the Museum of Science…

    Address

    6401 S Stony Island Ave, Chicago, IL 60637

    Nearest transit

    59th Street station (Metra Electric), 10-min walk

11. 11

    Starved Rock State Park - Canyons and the Illinois Foliage Trip

    Starved Rock State Park sits on the Illinois River about 95 miles southwest of Chicago and is the closest thing the region has to dramatic landscape: 18 sandstone canyons cut into the bluffs by glacial meltwater, with…

    Address

    2678 E 875th Rd, Oglesby, IL 61348

    Nearest transit

    No practical public transport; car required

From the trip1 travel guide “Chicago in Fall: Lakefront Colour and Festivals” · trip1.com