OBT-2

The OBT-2 is a 338-kilometre (210-mile) point-to-point trail encircling metropolitan Chicago, Illinois, United States, gaining approximately 580 metres of elevation across its glacially flat terrain. Accessible to hikers of moderate fitness and completable in 16–22 days, this Regional Walking Network route links forest preserves, prairies, wetlands and lakefront greenways in one of North America's most ambitious urban long-distance hiking systems.

About the OBT-2

The OBT-2 — the Chicago Outerbelt Trail — stretches 338 km through the greater Chicago metropolitan area, starting at Clarence B. Buckingham Memorial Fountain in Grant Park and winding through 41 mapped sections before finishing back at the North Side lakefront. Its designation within the Regional Walking Network (RWN) reflects its significance as a major regional corridor rather than a local footpath. Managed by the Outerbelt Alliance NFP, the route is a grassroots achievement: a community-built trail stitched together through a patchwork of county forest preserves, state conservation areas, city parks, and trail easements.

Unlike classic wilderness trails, the Chicago Outerbelt is defined by the contrast between urban grit and genuine natural beauty. Hikers pass through industrial heritage sites along the Calumet River, cross vast prairie grasslands south of the city, descend into the dense hardwood forests of the Palos Hills, follow the wooded corridor of the Des Plaines River north, and return along the shores of Lake Michigan. The result is a surprisingly varied route that rewards thru-hikers and section hikers alike.

Trail surfaces shift constantly — expect paved lakefront paths, compacted limestone multi-use trails, gravel forest preserve roads, grass track, and occasional stretches of road shoulder. Navigation relies on the official downloadable section maps (PDFs, sections 1–41) available from the Outerbelt Alliance, supplemented by onX Maps or trail resources from the Forest Preserve District of Cook County, which manages large portions of the route's central and western segments.

The Outerbelt is open to hikers, trail runners, and cyclists on shared-use sections. No single agency manages the entire corridor, which gives the OBT-2 an authentic, independently maintained character that larger, more heavily resourced long-distance trails sometimes lack. That also means conditions can vary — active trail monitoring by the Alliance community is the most reliable source of up-to-date section status.

Route Overview & Stages

The OBT-2 is divided into 41 named sections. For planning purposes, thru-hikers typically group these into six day-stages of 35–65 km, completing the full 338 km in 16–22 days. The table below reflects common groupings used by section hikers; distances are approximate given ongoing route refinements by the Outerbelt Alliance.

Highlights & Points of Interest

• Buckingham Fountain, Grant Park — The iconic Art Deco fountain marks the southern lakefront trailhead. Surrounded by Grant Park lawns and the Museum Campus, it provides a grand urban launch point for the full 338-km journey.
• Steelworkers Park & Big Marsh — A reclaimed industrial brownfield on the Calumet River, now a haven for migratory birds. The elevated berm trail offers panoramic views of the Chicago skyline that few visitors ever discover.
• Calumet Lake & Burnham Prairie — One of the finest remnant tallgrass prairies in Illinois, covering 267 hectares. Spring wildflower blooms and dramatic summer thunderstorm skies make this a photographic standout of the south section.
• Old Plank Trail — A 24-km paved multi-use corridor following an 1830s plank road through the south suburbs. Flat, fast, and well-signed, it covers ground quickly and offers several easy bail-out points to Metra stations.
• Palos Hills Forest Preserve — The most topographically dramatic section of the entire OBT-2. Oak and hickory forest on glacial ridges rises 30–40 metres above the surrounding flatlands, creating genuine woodland solitude just 25 km from downtown Chicago.
• Cal-Sag Channel — A 42-km engineered waterway completed in 1922 to reverse the flow of the Calumet River. The trail follows the industrial towpath in an atmosphere that is entirely unlike the forest preserve sections.
• Des Plaines River Trail — A 55-km greenway following the river north through Cook County forest preserves. Expect white-tailed deer, great blue herons, and mature bottomland hardwood forest at every season.
• Lake Michigan Lakefront Path — The final stretch follows one of the world's most celebrated urban waterfronts. On clear autumn days, the downtown skyline reflected in the lake is a fitting finale for a 338-km journey that began at its southern shore.

Best Time to Hike the OBT-2

Chicago's continental climate delivers hot humid summers, meaningful winter snowfall, and variable spring and autumn conditions. The OBT-2 has no high-mountain section that closes seasonally, but comfort, trail surface quality, and safety vary considerably across the calendar.

Spring (April–May): Wildflowers peak in late April and May, especially across Burnham Prairie and the Palos Hills understory. Daytime temperatures of 10–18 °C make for comfortable hiking. The downside is mud on grass sections and occasional trail flooding along the Des Plaines River floodplain after snowmelt.

Summer (June–August): Longest daylight hours, but heat and humidity can be punishing. July averages 29 °C with high relative humidity. Start before 7 a.m. on urban sections, carry at least 2 litres of water between resupply points, and be aware that urban heat islands on the south side make exposed asphalt stretches feel significantly hotter than the forecast temperature.

Autumn (September–October): The premier season for thru-hiking the OBT-2. Temperatures of 12–22 °C, substantially lower humidity than summer, and peak fall foliage — particularly in the Palos Hills hardwood forest and along the Des Plaines River corridor — create near-ideal conditions. Trail surfaces are at their firmest and city crowds thin sharply after Labor Day.

Winter (November–March): Not recommended for thru-hiking. Ice on paved sections is hazardous, some forest preserve facilities close, and sub-zero wind chills are common in January and February. Short day-hike sections are feasible for experienced cold-weather hikers with appropriate gear.

As of 2026, the Outerbelt Alliance recommends planning your thru-hike for late September through mid-October. The single best month is October, combining reliable cool temperatures with peak colour across the Palos Hills and Des Plaines River sections — the two most scenic stretches of the entire route.

Practical Information

Accommodation

The OBT-2 passes through a densely populated metropolitan area, so accommodation is plentiful — but there are no dedicated trail huts or hikers' hostels along the route itself. Thru-hikers typically combine the following options:

• Campgrounds: Several Cook County Forest Preserve sites accept tent campers, including campgrounds in the Palos Hills area (approx. €15–25 per night). Reservations are strongly recommended May–September when sites fill quickly.
• Budget motels & hotels: Available in every major suburb along the route. Rates in the south and west suburbs average €55–85 per night; last-minute booking platforms regularly show deals under €60.
• Downtown Chicago hostels: Several well-rated options in the Loop and Near North Side (€25–40 per dorm bunk) are ideal for the trailhead and finish days.
• Trail hosts: The Outerbelt hiking community is active online; the Alliance maintains a contact list of community members willing to offer floor space at key points along the route for thru-hikers.

Water resupply is reliable throughout — gas stations, park facilities, and convenience stores are rarely more than 8–10 km apart on any section of the trail.

Getting There & Back

The trail begins at Buckingham Fountain in Grant Park, served by multiple CTA bus lines and an 8-minute walk from the Roosevelt CTA Red/Green/Orange Line station. Chicago O'Hare International Airport (ORD) lies 30 km to the northwest; Chicago Midway Airport (MDW) is 14 km to the southwest — both have direct CTA rail connections to Grant Park in 45–65 minutes.

The trail's northern lakefront terminus is accessible via CTA Red Line stations at Loyola or Howard. Many thru-hikers drop a car at the finish and take the CTA to the start, or book a one-way Metra train back into the city after completing the route. Metra's Rock Island, Heritage Corridor, and UP-N lines all intersect the OBT-2 at multiple points, making stage bail-outs and resupply trips by public transport straightforward across almost every section.

Permits & Fees

No permit is required to hike the OBT-2. The trail crosses public lands managed by the Cook County Forest Preserves, Will County Forest Preserves, and the Illinois Department of Natural Resources — all free to access on foot. Some picnic area facilities within individual forest preserves charge a small reservation fee of €10–20 for group use; check the relevant preserve websites before booking. There is no registration system, thru-hiker fee, or trail pass for the route itself.

Gear & Packing List

The OBT-2's flat terrain and frequent urban resupply opportunities mean you can hike noticeably lighter than on remote backcountry routes. Carrying a single day's food supply between towns is usually sufficient — you will rarely need to haul more than 1.5–2 kg of food at once, which changes the pack-weight calculation dramatically compared to wilderness thru-hikes.

Footwear: Trail runners or lightweight hiking shoes with moderate grip suit the mixed surfaces best. Waterproof versions are worth the weight penalty for April–May starts when grass sections and forest preserve paths stay wet for days after rain.

Backpack: A 35–55-litre pack is ideal for multi-night carries. The Hyperlite Mountain Gear 2400 Windrider (1,130 g) is an excellent ultralight choice for this style of trail where resupply is easy and gram-counting pays off over 338 km. Those wanting a more structured carry should look at the Osprey Aether 65 for maximum comfort on heavier multi-night loads, or the Deuter Aircontact Lite 45+10 as a reliable mid-weight option with strong back ventilation for warm-weather hiking. For a broader comparison before you commit, see our roundup of the best ultralight backpacks of 2026.

Shelter: A freestanding tent or tarp-bivy is required for campground nights. Weight matters on this trail — you are covering urban pavement as well as forest track, and the cumulative toll of extra kilograms is felt acutely over the 16–22-day duration.

Navigation: Download all 41 official section maps from the Outerbelt Alliance before departure. onX Maps with offline caching is highly recommended as a backup, particularly for the southern urban sections where signage can be inconsistent.

Food & calories: Daily calorie needs on flat long-distance terrain typically run 2,500–3,500 kcal depending on pace and body weight. Read our guide on how many calories you need hiking a full day to calibrate food carry weight accurately before your start date.

Safety: Some southern sections of the OBT-2 pass through urban neighbourhoods where situational awareness is warranted. Keep valuables out of sight, time those sections to daylight hours, and share a live-location link with emergency contacts before each day. A fully charged portable battery pack is essential — phone navigation across 41 sections drains batteries fast.

Similar Trails You Might Like

If the OBT-2's blend of urban immersion and natural corridor hiking appeals to you, the United States has a rich selection of long-distance routes to explore next. The Trans-Catalina Trail makes a natural comparison — another point-to-point thru-hike, this one crossing Catalina Island in Southern California. The Pacific Crest Trail and the Continental Divide National Scenic Trail (4,988 km) represent the country's marquee backcountry thru-hikes — the natural progression for anyone who catches the long-distance bug on the Outerbelt. For shorter but dramatically scenic outings, the combined South Kaibab Trail and North Kaibab Trail form the classic Grand Canyon Rim-to-Rim crossing; the Hidden Canyon trail in Zion and the Clouds Rest Trail and Panorama Trail in Yosemite deliver concentrated mountain drama in a single day. Peak-baggers should add the Mount Whitney Trail to their list — the summit at 4,421 metres is the highest point in the contiguous 48 states and a world apart from Chicago's lake plain.

Frequently Asked Questions

When is the best time to hike the OBT-2?

October is the single best month. Temperatures of 10–18 °C, significantly lower humidity than summer, and peak autumn colour in the Palos Hills and Des Plaines River sections combine for near-ideal conditions. September is a strong second choice. Avoid July and August unless you are comfortable starting before dawn and managing sustained urban heat across the southern sections, where asphalt-amplified temperatures can exceed 35 °C at midday.

How difficult is the OBT-2?

By technical standards, the OBT-2 is a moderate-difficulty long-distance trail. Chicago sits on a glacial lake plain with negligible relief outside the Palos Hills section, meaning cumulative elevation gain is only around 580 metres across the full 338 km. The primary challenge is distance and urban navigation, not altitude or rugged terrain. Hikers with a few multi-day backpacking trips of experience can tackle the route; the main demand is sustained daily mileage and the mental endurance of a 16–22-day undertaking.

How many kilometres per day should I plan?

Most thru-hikers cover 18–25 km per day, completing the 338 km in 16–20 days. The flat terrain makes higher daily mileage more sustainable than on mountain routes. Stronger hikers doing 28–30 km days can finish in 12–14 days. Factor in slower pacing through dense urban areas where road crossings, navigation, and resupply stops add time. The Old Plank Trail (Stage 2) and the Des Plaines River Trail (Stage 5) are the fastest-moving stretches on the route.

What accommodation is available along the trail?

Options range from Cook County Forest Preserve campgrounds (€15–25 per night; advance booking recommended May–September) to budget motels in the south and west suburbs (€55–85 per night). Downtown Chicago hostels cover the trailhead and finish days at €25–40 per dorm bunk. There are no dedicated trail huts or mountain-style shelters on the OBT-2. Water resupply is reliable throughout — shops, parks, and gas stations are typically within 10 km on every section of the route.

Do I need a permit to hike the OBT-2?

No permit is required. The OBT-2 crosses free-to-access public lands managed by Cook County Forest Preserves, Will County Forest Preserves, and the Illinois Department of Natural Resources. There is no registration fee, trail pass, or camping permit for the route itself. Specific group picnic facilities within forest preserves may require a small reservation fee of €10–20, but ordinary hiking and tent camping on designated sites are entirely free of charge.