Solo trips from Chicago
Easy places to go on your own from Chicago: walkable cities with good transit, social hostels and plenty to do alone. Each has the cheapest round trip we've seen recently.
The cheapest matching round trip we’ve seen recently for each destination.
Cheapest right now: Portland $264 · Montreal $301 · Vancouver $455
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Fares observed October 8 – 14, 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 | |
|---|---|---|---|---|
| Lisbon (LIS) | Social hostels, free walking tours and trams up to the miradouros | $691 (airline $729) | Feb 1–Mar 3, 2027 | Check prices |
| Tokyo (HND) | Counter-seat ramen and sushi bars made for one, and trains that run to the minute | $1,286 (airline $1,357) | Nov 14–22, 2026 | Check prices |
| Copenhagen (CPH) | Flat, bike-friendly streets that feel safe late at night, and English widely spoken | $1,568 (airline $1,658) | Jun 25–Jul 4, 2027 | Check prices |
| Montreal (YUL) | Bilingual and walkable, with the metro, the Plateau's cafés and summer festivals | $301 (airline $318) | Dec 11–14, 2026 | Check prices |
| Reykjavik (KEF) | Day tours from Reykjavík to the Golden Circle and south coast make it easy alone | $597 (airline $629) | Nov 10–17, 2026 | Check prices |
| Seoul (ICN) | A subway that goes everywhere and a culture of eating out alone at honbap spots | $1,152 (airline $1,218) | Jan 30–Feb 13, 2027 | Check prices |
| Mexico City (MEX) | Walkable Roma and Condesa, group food tours and a metro across a huge city | $472 (airline $498) | Nov 21–23, 2026 | Check prices |
| Amsterdam (AMS) | Cycle anywhere, stay in a social hostel and meet people on a canal walk | $789 (airline $835) | Nov 24–Dec 1, 2026 | Check prices |
| Edinburgh (EDI) | A compact Old Town on foot, pubs with live folk music and free walking tours | $808 (airline $854) | Nov 10–17, 2026 | Check prices |
| Singapore (SIN) | Hawker centers with single seats, a spotless MRT and very low crime | $952 (airline $1,004) | Jan 30–Feb 13, 2027 | Check prices |
| Taipei (TPE) | Night markets for grazing solo, an easy MRT and streets that feel safe after dark | $911 (airline $961) | Nov 10–17, 2026 | Check prices |
| Melbourne (MEL) | A free tram zone in the city, laneway cafés and an easygoing pub scene | $1,402 (airline $1,484) | Nov 10–17, 2026 | Check prices |
| Vancouver (YVR) | SkyTrain from the airport, the Stanley Park seawall and hostels downtown | $455 (airline $481) | Feb 12–16, 2027 | Check prices |
| Medellin (MDE) | El Poblado's hostels, the metro and cable cars, and Comuna 13 walking tours | $465 (airline $491) | Feb 1–Mar 3, 2027 | Check prices |
| Portland (PDX) | Food cart pods, Powell's Books and MAX light rail straight from the airport | $264 (airline $278) | Nov 10–17, 2026 | Check prices |
| Barcelona (BCN) | Gothic Quarter walks, beach days at Barceloneta and hostels with group dinners | $681 (airline $718) | Jun 2–6, 2027 | Check prices |
| Chiang Mai (CNX) | Old City temples, cooking classes and a big community of travelers and remote workers | $838 (airline $883) | Feb 1–Mar 3, 2027 | Check prices |
| Berlin (BER) | Hostels, bar-hopping in Kreuzberg and a U-Bahn that runs all night on weekends | No matching fare saved | Search other dates | |
| Dublin (DUB) | Pubs where strangers chat over trad music sessions, and a city easy to cross on foot | $653 (airline $690) | Nov 13–22, 2026 | 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
Check your government's travel advice before you go; it can differ from one city or region to the next.
Facts checked October 7, 2026. Sources: Wikipedia: Melbourne's Free Tram Zone
Keep exploring
Hotels in Lisbon with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Lisbon has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Solo trips from Chicago. The best places to travel alone from Chicago: Lisbon, Tokyo, Copenhagen, Montréal, Reykjavík, Seoul, Mexico City, Amsterdam, Edinburgh, Singapore, Taipei and more, with real round-trip fares.
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https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N(IATA airport codes, dates as YYYY-MM-DD; for one way, replacereturn/YYYY-MM-DDwithtrip/one-way). - If a link can no longer be opened: search for "Axel Solo trips from Chicago" and open the result; the Flight search guide is always findable by search, and everything here works without an account, API key or connector. Or ask the traveler to open https://helloaxel.com/en/flights/from-chicago-solo-trips; an address the traveler opens always works.
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