Chicago Marathon

October timing note: Mid-October in Chicago coincides with peak fall foliage in the upper Midwest. The post-race travel options to Wisconsin and Indiana are at their most scenic in this specific window.

Alternative routes: Charity places and international tour operator packages with guaranteed entry are available for runners who do not receive a ballot place.

The Expo: Thursday to Saturday

The Chicago Marathon expo takes place at McCormick Place, Chicago's convention centre on the South Side, Thursday to Saturday before race Sunday. Number collection is at the expo; there is no race-day collection. The CTA Red Line to Cermak-McCormick Place or a taxi from the Loop takes 10 to 15 minutes. Allow 90 minutes at the expo.

Race Day Morning

The start in Grant Park is walkable from most central hotels. Wave starts run from approximately 07:30. Arrive at least 60 minutes before your wave; the corrals can be congested. The October morning temperature in Grant Park is typically cool; bring a throwaway layer and discard it at the start line.

The Course

The route runs west and south from Grant Park through the Loop, River North, Chinatown, Bridgeport, and the South Side neighbourhoods before returning north through the Near South Side and finishing on Columbus Drive in Grant Park. Crowd support is dense throughout, particularly in Wrigleyville around km 24 and in the final stretch back to the park.

After Finishing

The finish and recovery area are in Grant Park. Most central hotels are within comfortable walking distance. The finish area is large and disperses efficiently; the CTA Blue and Red Lines are immediately adjacent for those further from the park.

CTA Purple Line Express from the Loop · 35 min · $2.50 · no hire car · direct taxi to O'Hare

The CTA Purple Line Express runs from any downtown Loop station to Evanston in 35 minutes, fare $2.50. Get off at Davis Street - the most central stop for the lakefront and Northwestern University. Evanston is the first substantial suburb north of Chicago's city limits: a flat glacial plain on Lake Michigan, 75,000 people, in full fall colour by mid-October.

Northwestern University's lakefill - campus built on fill land that extended the original shoreline eastward - has a flat paved path running approximately 1.5 kilometres at the water's edge. October: dark blue-grey water, the beginning of the winter chop, the Chicago skyline visible to the south. Walk to the observatory promontory and back. The Grosse Point Lighthouse at the northern end of the lakefill is a National Historic Landmark, built in 1873 after the ship Lady Elgin sank off this shore in 1860 with 300 passengers aboard. The grounds are accessible; weekend tours are available at grossepointlighthouse.net.

The Davis Street corridor has a good concentration of independent restaurants within a 10-minute flat walk of the lakefront. Farmhouse Evanston on Grove Street is the local benchmark for Midwest farm-sourced cooking; Peckish Pig on Davis Street is the craft beer and gastro-pub option. Return to O'Hare by taxi or rideshare (35 to 45 minutes, $35 to $50), or take the CTA Purple Line to Howard and transfer to the Red Line (approximately 60 minutes, considerably cheaper).

South Shore Line from Millennium Station · 65 min · ~$10–12 · no hire car required

The South Shore Line commuter rail runs from Millennium Station (under Millennium Park, entrance at 151 E. Randolph) to Dune Park station in 65 minutes, with trains roughly every 30 to 60 minutes; fare approximately $10 to $12. From Dune Park, a short taxi (approximately $8) reaches the park visitor centre. Indiana Dunes National Park covers 24 kilometres of Lake Michigan shoreline in northwest Indiana: moving sand dunes, oak savannas, bogs, and the Great Marsh, one of the largest remaining Great Lakes wetlands.

The Great Marsh Trail is the post-marathon walking infrastructure. Level throughout - wide, compacted earth, firm in October - it follows the marsh perimeter through sedge meadows, willow thickets, and open water, approximately two kilometres each way from the main trailhead. October is peak migration through the Lake Michigan bottleneck corridor: tens of thousands of raptors, songbirds, and waterfowl move through the dune and marsh landscape in a way that summer visits simply are not. The tall sand dunes that give the park its name involve significant climbing and are not the post-marathon programme.

The Century of Progress Architectural District within the park contains homes from the 1933--34 Chicago World's Fair, relocated to the dunes after the exposition closed - modernist experimental designs by George Fred Keck and others, accessible from the exterior year-round. Stay in Chesterton (adjacent to Dune Park station), where the Gray Goose Inn is the small-hotel option and Octave Wine Bistro is the dinner recommendation. Return: South Shore Line to Millennium Station (65 minutes), then CTA Blue Line to O'Hare (approximately 45 minutes).

Amtrak Hiawatha from Chicago Union Station · ~90 min · from $19 · no hire car required

Leave the car at home. The Amtrak Hiawatha runs from Chicago Union Station directly to Milwaukee Intermodal Station in around 90 minutes, with up to six departures a day. Union Station is on the west side of downtown Chicago and straightforward to reach from the Grant Park finish area by rideshare. Take the afternoon train the day after the race, check in, and walk the Historic Third Ward - Milwaukee's converted warehouse district along the Milwaukee River, flat, with the city's best independent restaurants and the covered Milwaukee Public Market.

The second day is the full Milwaukee day. Start at the Milwaukee Art Museum (700 N Art Museum Dr) before the crowds arrive. The building is Santiago Calatrava's Quadracci Pavilion, completed in 2001 - a white wing structure on the Lake Michigan waterfront that opens and closes its moveable brise-soleil twice a day. From outside it looks like a ship about to sail. Inside, the collection runs to 32,000 works and the lakefront views from the upper galleries are among the best in any American museum. Allow two hours.

Two miles southwest of the art museum, the Harley-Davidson Museum (400 W Canal St) covers 20 acres along the Menomonee River with over 450 machines on display from the first Harley built in 1903 to current production models. The early machines - assembled in a 10-by-15-foot shed behind the Davidson family home - are extraordinary objects to stand next to. The MOTOR Bar on site is a solid lunch stop. Lakefront Brewery (1872 N Commerce St), in a former Milwaukee pumping station on the Milwaukee River, has been doing guided tours and tastings since 1987; the Friday fish fry is a Wisconsin institution, but any day works.

If the Milwaukee Bucks are playing during your visit - the NBA season runs from October - a ticket to a game at Fiserv Forum is a genuinely good evening in a city that lives for its team. Even without a game, the Deer District bars and restaurants are lively and the arena is worth seeing. Two nights in Milwaukee is the right amount of time. The Hiawatha runs back to Chicago Union Station with up to six departures daily from early morning to late evening.

Hire car from O'Hare · 330 miles total · O'Hare drop-off on return from Milwaukee

Nights 1 and 2: The Illinois River Valley

Pick up the car at O'Hare - the airport sits on the northwest edge of the city and puts you directly on I-88 heading west. The drive to Oglesby takes around 90 minutes. Starved Rock State Park has 18 canyons carved by glacial meltwater into St. Peter sandstone: walls streaked with ochre, green, and rust mineral deposits, ferns growing from every crevice, and several waterfalls that run well into autumn after rains. The park receives over a million visitors a year; on weekdays the canyons are largely empty.

Do not hike the first evening. The flat Riverview Trail along the top of the bluffs is enough. The canyons require stairs, steep descents, and uneven footing - French Canyon alone descends 150 stone steps to the floor. Two days after a marathon this is genuinely good active recovery, but go slowly, use the handrails, and wear shoes with grip. The short loop from the Visitor Centre through French Canyon and Wildcat Canyon covers around two miles. Extending east to LaSalle Canyon adds the park's tallest waterfall. In mid-October, cottonwoods, oaks, and maples line the bluffs in full colour.

Matthiessen State Park is three miles south on Route 178 and receives a fraction of Starved Rock's visitors despite being equally beautiful. The Dells Area trail descends via boardwalk and stone steps to Cascade Falls, where the canyon drops 45 feet into a pool. The walk from the parking lot to the main waterfall is around 10 minutes on more level terrain than Starved Rock's busier trails, which makes it the better choice for post-race legs. The full Dells loop is around two miles. Between the two parks, expect four to six miles over the day with frequent stops.

Day 3: Lake Geneva, then north to Milwaukee

The drive from Oglesby north to Lake Geneva takes around 90 minutes on US-34. You cross into Wisconsin somewhere around Genoa City and the landscape shifts: more farmland, more dairy barns, Holstein herds visible from the road. Lake Geneva sits on the southern shore of Geneva Lake, a glacier-formed lake that has been a retreat from Chicago summer heat since the 1870s. The grand estates along the shoreline were built by the families whose names are still on Chicago buildings - Wrigley, Schwinn, Montgomery Ward - and some of those houses are still there, glimpsed through mature trees as you walk the shore path.

The Geneva Lake Shore Path runs 21 miles around the full lake. For post-marathon legs, two to four miles along the town waterfront is the right section: minimal gradient, alternating between concrete, gravel, and packed earth, the water close enough to feel throughout. The lake is still and deep blue in October, and the crowds are thinner than in summer. Pick up the path at Riviera Docks in the town centre and walk in either direction. Lunch in downtown Lake Geneva before driving north: the food skews towards Wisconsin comfort - fish fry, cheese curds, hearty soups. The drive from Lake Geneva to Milwaukee takes 45 minutes on I-43.

Nights 3 and 4: Milwaukee

Milwaukee rewards a slower look than most visitors give it. Start the first morning at the Milwaukee Art Museum before the crowds arrive. The Calatrava Quadracci Pavilion opens and closes its moveable brise-soleil twice a day; from outside it looks like a ship preparing to sail. Allow two hours for the collection and the Lake Michigan views from the upper galleries. The Harley-Davidson Museum (400 W Canal St) is two miles southwest: 20 acres along the Menomonee River, 450 machines from the first Harley of 1903 to current production. The early machines - assembled in a 10-by-15-foot shed - are extraordinary objects to stand next to. Lakefront Brewery (1872 N Commerce St), in a former city pumping station, does the best guided tour in Milwaukee.

If the Bucks are playing, a game at Fiserv Forum is a good evening in a city that lives for its team - the NBA season runs from October so the timing works. The Historic Third Ward, Milwaukee's converted warehouse district, is the right place for the final afternoon: flat, walkable, independent restaurants and the Milwaukee Public Market under one roof. Return the car to O'Hare via I-94 east; the drive takes around 90 minutes. Leave Milwaukee by mid-afternoon if you have an evening flight.