Mountain and trekking trips from Chicago

Fly from Chicago to the airports closest to the world's best treks and mountain walks, each with the cheapest round trip we've seen recently. The reason under each one says which trail it gets you to.

The cheapest matching round trip we’ve seen recently for each destination.

Cheapest right now: Calgary $336 · Anchorage $486 · Reykjavik $517

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Flights from Chicago

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Mountain and trekking trips from other cities

Fares observed October 7 – 9, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Chicago

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goAxelDates
Cuzco (CUZ)The Inca Trail and the Salkantay trek to Machu Picchu, both starting a few hours from Cusco$1,173 (airline $1,240)Mar 20–24, 2027Check prices
Kathmandu (KTM)Everest Base Camp via a flight to Lukla, and the Annapurna treks from Pokhara$1,537 (airline $1,621)Nov 10–17, 2026Check prices
Kilimanjaro (JRO)Kilimanjaro's Machame and Lemosho routes start about an hour from the airport, by way of Moshi$1,098 (airline $1,157)Nov 10–17, 2026Check prices
Geneva (GVA)The Tour du Mont Blanc from Chamonix, about an hour from Geneva by road$661 (airline $698)Nov 10–17, 2026Check prices
Zurich (ZRH)Zermatt and the Matterhorn, the end of the Haute Route from Chamonix, about 3.5 hours by train$654 (airline $692)Nov 10–17, 2026Check prices
Munich (MUC)The Bavarian Alps at Garmisch and Berchtesgaden, and Innsbruck's Nordkette, about 2 hours away$733 (airline $773)Dec 3–7, 2026Check prices
Venice (VCE)The Dolomites' Alta Via 1 from Lago di Braies, and Cortina d'Ampezzo, about 2 hours north$601 (airline $635)Dec 8–15, 2026Check prices
Ljubljana (LJU)Triglav National Park: the Seven Lakes Valley and the climb to Slovenia's highest peak$806 (airline $849)Nov 10–17, 2026Check prices
Bergen (BGO)Trolltunga and the Hardangerfjord trails, about 3 hours east of Bergen$705 (airline $745)Nov 10–17, 2026Check prices
Calgary (YYC)Banff's Lake Louise and Sunshine Meadows trails, and the Icefields Parkway to Jasper$336 (airline $354)Dec 8–15, 2026Check prices
Reykjavik (KEF)The Laugavegur trail between Landmannalaugar and Thórsmörk, and Fimmvörðuháls over to Skógar$517 (airline $546)Nov 10–17, 2026Check prices
Santiago De Compostela (SCQ)The end of the Camino de Santiago; the last 100 km from Sarria earns a Compostela$743 (airline $783)Nov 10–17, 2026Check prices
Cape Town (CPT)Table Mountain's Platteklip Gorge, and the Otter Trail along the Garden Route, about 6 hours east$1,212 (airline $1,276)Nov 10–17, 2026Check prices
Osaka (KIX)The Kumano Kodo pilgrimage trails in Wakayama, about 3 hours south of Osaka$1,329 (airline $1,404)Aug 7–14, 2027Check prices
Anchorage (ANC)The Chugach trails above the city, and Kenai Fjords' Harding Icefield trail, 2.5 hours south$486 (airline $513)Nov 10–17, 2026Check prices
Queenstown (ZQN)The Routeburn Track and Ben Lomond from Queenstown, and the Milford Track from Te Anau$1,266 (airline $1,337)Dec 8–15, 2026Check prices

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

About these places

Permits for the Inca Trail and the Milford Track sell out months ahead, and Kilimanjaro climbs must be guided. For Yellowstone, Zion, Glacier and the other US parks, see national park trips.

Facts checked October 8, 2026.

Keep exploring

Hotels in Cusco with Axel

Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Cusco has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.

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