Graduation trips from Chicago
A trip to mark graduation from Chicago, for the grad, the friend group or the whole family: fares for a week from Saturday, June 5 and a week from Saturday, June 19, 2027, once most schools and colleges have let out.
Saved round trips for First week of June 2027 (Jun 5 – Jun 12, 2027) and Third week of June 2027 (Jun 19 – Jun 26, 2027).
Cheapest right now: San Juan $262 · Mexico City $299 · Las Vegas $314
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Fares observed October 10 – 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 | |
|---|---|---|---|---|
| Cancun (CUN) | All-inclusive beach clubs in the Hotel Zone, Coco Bongo nights and a day trip to Tulum or Isla Mujeres | $514 (airline $542) | Jun 19–26, 2027 | Check prices |
| Punta Cana (PUJ) | Bávaro's all-inclusives with swim-up bars, a Saona Island catamaran day and Coco Bongo Punta Cana | $367 (airline $386) | Jun 19–26, 2027 | Check prices |
| Nassau (NAS) | Cable Beach, Atlantis's water park on Paradise Island and the Fish Fry at Arawak Cay, an easy first trip abroad | $620 (airline $655) | Jun 5–12, 2027 | Check prices |
| Montego Bay (MBJ) | Doctor's Cave Beach, all-inclusives along the Hip Strip and cliff jumps at Rick's Café in Negril | $477 (airline $504) | Jun 5–12, 2027 | Check prices |
| Las Vegas (LAS) | Pool parties, the Sphere and Strip shows for 21-plus grads, with Red Rock Canyon or Grand Canyon West by day | $314 (airline $331) | Jun 5–12, 2027 | Check prices |
| Miami (MIA) | South Beach by day and clubs in Wynwood and Brickell by night, with the Keys a road trip away | $373 (airline $395) | Jun 5–12, 2027 | Check prices |
| Oahu / Honolulu (HNL) | Waikiki surf lessons, the Diamond Head hike and North Shore shrimp trucks, with Pearl Harbor for the family trip | $716 (airline $757) | Jun 19–26, 2027 | Check prices |
| San Juan (SJU) | Old San Juan's forts and street parties, El Yunque rainforest and Condado beach, no passport for US grads | $262 (airline $276) | Jun 5–12, 2027 | Check prices |
| Lisbon (LIS) | A walkable first trip abroad: Alfama's lanes, Bairro Alto's bars at night and Cascais beaches by train | $903 (airline $955) | Jun 19–26, 2027 | Check prices |
| Barcelona (BCN) | Barceloneta beach, Gaudí and late-night bars in El Born, with Sitges and the Costa Brava nearby | $848 (airline $895) | Jun 19–26, 2027 | Check prices |
| Athens (ATH) | The Acropolis and Plaka, then ferries to Mykonos or Santorini for the beach-club half of the week | $703 (airline $742) | Jun 19–26, 2027 | Check prices |
| Amsterdam (AMS) | Bikes, canals and the Van Gogh Museum by day, with Leidseplein and Rembrandtplein nightlife | $1,039 (airline $1,099) | Jun 19–26, 2027 | Check prices |
| Dublin (DUB) | Temple Bar's pubs for the 18-plus crowd, the Guinness Storehouse and a day out to the Cliffs of Moher | from $879 (airline $926) | Jun 5–12, 2027 | Check prices |
| Paris (CDG) | The Louvre, the Eiffel Tower and a Seine cruise for the family trip, with Le Marais and Oberkampf bars at night | $795 (airline $837) | Jun 5–12, 2027 | Check prices |
| Rome (FCO) | The Colosseum, the Vatican and Trastevere's gelato and bars, a walkable first stop on a Europe trip | $799 (airline $846) | Jun 19–26, 2027 | Check prices |
| Mexico City (MEX) | Roma Norte and Condesa cafés and bars, the Frida Kahlo museum and the pyramids at Teotihuacán | $299 (airline $316) | Jun 19–26, 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
Age rules differ: the US drinking age is 21, most of the countries here set it at 18, and some resorts and beach clubs are adults-only. Hawaii and Puerto Rico need no passport for US citizens; everywhere else does, and Canadians need one for every destination here.
Facts checked October 8, 2026.
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For AI assistants
- This page: Graduation trips from Chicago. Graduation trips from Chicago for the class of 2027: Cancún, Punta Cana, Nassau, Montego Bay, Las Vegas, Miami, Honolulu, San Juan, Lisbon, Barcelona, Athens, Amsterdam, Dublin, Paris, Rome and Mexico City, with fares for the first and third weeks of June, right after high school and college commencements.
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