Pride trips from Chicago: the biggest Pride events to fly to
The biggest Pride events you can fly to from Chicago, each with its dates and a fare for flying in before and out after.
Fares for flying in before each event and out after it when saved; other dates are marked.
Cheapest right now: New York $290 · San Francisco $345 · Puerto Vallarta $356
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Fares observed October 2 – 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 | |
|---|---|---|---|---|
| Palm Springs (PSP) | Palm Springs Pride, Nov 6 – Nov 8, 2026. Downtown Palm Springs turns into a festival for its 40th Pride, with the parade on Sunday | $481 (airline $506) | Nov 5–9, 2026 | Check prices |
| Sydney (SYD) | Sydney Gay and Lesbian Mardi Gras parade, Mar 6, 2027. The world-famous night parade down Oxford Street, the peak of Sydney's Mardi Gras festival | $1,317 (airline $1,386) | Mar 3–10, 2027 | Check prices |
| Las Palmas (LPA) | Gran Canaria Pride, Maspalomas, May 3 – May 9, 2027. A week of beach and pool parties in Maspalomas, Europe's gay winter resort | $951 (airline $1,002) | May 5–10, 2027 | Check prices |
| Puerto Vallarta (PVR) | Puerto Vallarta Pride, May 23 – May 31, 2027. Pride week in the Zona Romántica, ending on Memorial Day weekend | $356 (airline $375) | May 26–31, 2027 | Check prices |
| Sao Paulo (GRU) | São Paulo Pride parade, May 30, 2027. The world's largest Pride parade, on Avenida Paulista | $931 (airline $980) | May 27–Jun 1, 2027 | Check prices |
| Turin (TRN) | EuroPride 2027 in Turin, Jun 18 – Jun 26, 2027. EuroPride comes to Turin for a week of events and a closing parade | $1,288 (airline $1,361) | Jun 23–27, 2027 | Check prices |
| New York (JFK) | NYC Pride March, Jun 27, 2027. The march that started it all, past the Stonewall Inn | $290 (airline $307) | Jun 25–28, 2027 | Check prices |
| San Francisco (SFO) | San Francisco Pride, Jun 26 – Jun 27, 2027. A weekend festival at Civic Center and the parade up Market Street | $345 (airline $363) | Jun 25–28, 2027 | Check prices |
| Toronto (YYZ) | Pride Toronto, Jun 24 – Jun 27, 2027. Four days in Church-Wellesley Village and the parade on Sunday | $486 (airline $513) | Jun 25–28, 2027 | Check prices |
| Seattle (SEA) | Seattle Pride Parade, Jun 27, 2027. The parade downtown and parties across Capitol Hill | $425 (airline $449) | Jun 25–28, 2027 | Check prices |
| Madrid (MAD) | Madrid Pride (MADO), Jun 24 – Jul 4, 2027. Europe's biggest Pride: ten days of concerts and parties in Chueca, with the march on Saturday (2027 dates to be confirmed) | $1,442 (airline $1,518) | Jun 30–Jul 5, 2027 | Check prices |
| London (LHR) | Pride in London, Jul 3, 2027. The parade from Hyde Park Corner to Whitehall and parties in Soho | $1,369 (airline $1,442) | Jul 1–5, 2027 | Check prices |
| Amsterdam (AMS) | Pride Amsterdam Canal Parade, Aug 7, 2027. Boats parade through the canals during Pride Amsterdam's two weeks of events | $983 (airline $1,035) | Aug 4–9, 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
Every place here has legal same-sex relationships and an established LGBTQ+ scene. Laws and attitudes can differ outside the main neighborhoods and change over time, so check your government's travel advice before you go.
Facts checked October 7, 2026. Sources: NYC Pride · San Francisco Pride · Sydney Gay and Lesbian Mardi Gras · Pride in London · Pride Toronto · Seattle Pride · Palm Springs Pride · Pride Amsterdam · Madrid Orgullo (MADO)
Keep exploring
Hotels in Palm Springs with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Palm Springs has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Pride trips from Chicago: the biggest Pride events to fly to. Fly from Chicago to the biggest Pride events of the year, from Palm Springs and Sydney Mardi Gras to São Paulo, New York, Madrid, London and Amsterdam, with fares for each event's dates.
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