Dublin
United
Flight duration: 7.5 hours
Departure: Daily at 6:05 p.m.
Fare: From $906
High note: New summer service (June 4 to August 17) means more competition for American and Aer Lingus (translation: maybe an occasional sale) and more miles for United MileagePlus members.
Why go now: Ireland is celebrating the 150th anniversary of the birth of the Nobel Prize–winning poet William Butler Yeats this year (yeats2015.com). View the collection of his work at the National Library of Ireland, and take a backstage tour of the Abbey Theatre, which the poet cofounded. And on June 16, relive the events of Ulysses on Bloomsday, the annual celebration of the Irish writer James Joyce.
Helsinki
Finnair
Flight duration: 9 hours
Departure: Mondays, Thursdays, and Saturdays around 10 p.m.
Fare: From $1,475
High note: The only direct flight available from Chicago, this seasonal offering (through October 17) earns travelers miles with Oneworld (an airline alliance that includes American). Business class travelers score an amenity kit from the Finnish design company Marimekko.
Why go now: It’s festival season. Check out Finland’s largest arts event, the annual Helsinki Festival (August 14 to 30, $40, helsinginjuhlaviikot.fi), or this summer’s concerts at the mod Helsinki Music Centre (June 8 to August 9, $40, stopover.fi), marking the 150th birthday of Finnish composer Jean Sibelius.
Rome
United
Flight duration: 9 hours
Departure: Daily at 6:20 p.m.
Fare: From $1,492
High note: United loyalists can finally skip the connections at Newark or Washington Dulles with this seasonal route (through September 23).
Why go now: The avant-garde decor of the new boutique hotel G-Rough, coupled with its unbeatable Piazza Navona location, makes it a must-stay. These 16th-century digs reek of Roman flamboyance (from $360, g-rough.com).
Dubai
Emirates
Flight duration: 13 hours
Departure: Daily at 8:30 p.m.
Fare: From $1,489
High note: This marks the first time Chicagoans can fly direct to Dubai on glamorous Emirates, with its multicourse meals and eight private first-class suites, no less.
Why go now: Brave summer’s heat, with highs in the triple digits, and you’ll up your chances of landing a coveted tee time under the stars for cooler, glitzy night golfing at the 18-hole Faldo course at the Emirates Golf Club (from $115, dubaigolf.com).
Savvy Traveler Tip
If you're returning to O'Hare from abroad, speed up your trip through customs with Mobile Passport, a free U.S. Customs and Border Protection app. Fill out your profile and submit your customs declaration forms electronically. Then take an express lane through customs, rather than waiting (and waiting) in line. O'Hare, which started using the app in April, is one of only four airports to offer the service. (The others are in Atlanta, Miami, and Seattle.)