Summer vacation trips from Chicago
Where to go from Chicago this summer: fares for seven nights from June through August, to coasts, islands, national parks and cities.
Saved round trips for 7 nights, entirely within Jun, Jul, Aug.
Cheapest right now: Montreal $422 · Calgary $431 · Jackson $436
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Fares observed October 8, 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.
| Destination | Why go | Axel | Dates | |
|---|---|---|---|---|
| Naples (NAP) | Naples is the ferry hub for Capri, Sorrento and the towns of the Amalfi Coast | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Thira (JTR) | Santorini's caldera sunsets in Oia and black-sand beaches at Perissa and Kamari | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Dubrovnik (DBV) | Dubrovnik's walled Old Town, swims off the rocks and boat trips to Lokrum island | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Split (SPU) | Split's Diocletian's Palace and ferries to the islands of Hvar, Brač and Vis | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Nice (NCE) | Nice's Promenade des Anglais and day trips along the Riviera to Èze, Monaco and Antibes | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Palma de Mallorca (PMI) | Mallorca's coves, the Serra de Tramuntana mountains and Palma's cathedral quarter | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Lisbon (LIS) | Lisbon's hilltop neighborhoods and the beaches of Cascais and Costa da Caparica | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Athens (ATH) | The Acropolis, then ferries from Piraeus to Paros, Naxos and the other Cyclades | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Reykjavik (KEF) | Iceland's long summer days, the Golden Circle and the waterfalls of the south coast | No matching fare saved | Jun 26 – Jul 3, 2027 (suggested) | Search these dates |
| Anchorage (ANC) | Denali, glacier cruises from Seward and Whittier, and Alaska's long summer days | $619 (airline $653) | Jul 24–31, 2027 | Check prices |
| Juneau (JNU) | Mendenhall Glacier, whale watching in Auke Bay and the fjords of the Inside Passage | $535 (airline $564) | Jun 26–Jul 3, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki, the Diamond Head hike and Oahu's North Shore in calm summer water | $633 (airline $670) | Jun 26–Jul 3, 2027 | Check prices |
| Maui / Kahului (OGG) | Maui's Road to Hana, sunrise on Haleakalā and the beaches of Kāʻanapali and Wailea | $714 (airline $754) | Jun 26–Jul 3, 2027 | Check prices |
| Kauai / Lihue (LIH) | Kauai's Nā Pali Coast, Waimea Canyon and the curve of Hanalei Bay | $455 (airline $481) | Aug 7–14, 2027 | Check prices |
| Kalispell (FCA) | Glacier National Park and the Going-to-the-Sun Road, about 30 minutes from the airport | $463 (airline $488) | Aug 7–14, 2027 | Check prices |
| Jackson (JAC) | Grand Teton's lakes and trails by the airport, with Yellowstone's south gate about an hour north | $436 (airline $461) | Jun 26–Jul 3, 2027 | Check prices |
| Vancouver (YVR) | Stanley Park, Granville Island and day trips to Whistler and Vancouver Island | $568 (airline $600) | Jun 26–Jul 3, 2027 | Check prices |
| Calgary (YYC) | Banff, Lake Louise and Moraine Lake in the Rockies, about 90 minutes west of Calgary | $431 (airline $455) | Jul 10–17, 2027 | Check prices |
| Montreal (YUL) | Old Montreal, the Plateau's terraces and the city's summer festival season | $422 (airline $446) | Jun 26–Jul 3, 2027 | Check prices |
| Quebec (YQB) | Old Quebec's walled city, the Plains of Abraham and Montmorency Falls | $590 (airline $624) | Jun 26–Jul 3, 2027 | Check prices |
| Tokyo (HND) | Tokyo's neighborhoods, summer fireworks festivals and day trips to Hakone and Nikko | $1,569 (airline $1,660) | Jul 10–17, 2027 | Check prices |
| Osaka (KIX) | Osaka's food streets, with Kyoto's temples and Nara's deer a short train ride away | $1,329 (airline $1,404) | Aug 7–14, 2027 | Check 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
Summer is peak season for every place here, so flights and rooms fill early. UK school dates vary by council, so check your school's calendar.
Facts checked October 7, 2026. Sources: Kent County Council: term dates 2026 to 2027 · Hampshire County Council: school holiday dates
Keep exploring
Hotels in Amalfi Coast with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Amalfi Coast has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Summer vacation trips from Chicago. Summer vacation flights from Chicago: Europe's coasts, Iceland, Alaska, Hawaii, national parks, Canada's cities and Japan, with fares for seven nights from June through August.
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