One of our favorite things about Chicago is that we can hop on a flight after work on Friday and be in a completely different world by dinnertime. So, if you’ve ever longed to see the Northern Lights, drink craft beer in Portland or go scuba diving off the coast of Mexico, let’s make these dreams a reality. We’ve found five short flights from Chicago to book ASAP.
5 Short Flights from Chicago That’ll Transport You to a Totally Unique Destination in Practically No Time
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Published Jul 20, 2023
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Iberostar Cozumel
Half Moon Jamaica
1. Montego Bay, Jamaica
- Flight Time from Chicago: 4 hours
- Why We Recommend It: gorgeous beaches, warm temperatures, great food
- Where to Stay: Round Hill Hotel and Villas (from $698); S Hotel Jamaica (from $669); Half Moon (from $482)
We’ll always love you, Chicago. But in January we’re packing our bags and heading to Montego Bay, where the average high is 84 degrees, not 32. The capital of Saint James Parish is packed with beach resorts, so you definitely won’t be the only tourist here, but sometimes you just have to order a rum punch and kick back in your cabana.
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2. Portland, Oregon
- Flight time from Chicago: 4 hours, 23 minutes
- Why We Recommend It: great food, awesome beer, cool neighborhoods
- Where to Stay: The Marc Spencer Hotel (from $187); Hotel Vance (from $166); Hotel Grand Stark (from $182)
Ever wish Logan Square were…bigger? Hop on a flight to Portland for 145 square miles of farm-to-table restaurants, craft breweries, beautiful old houses and easy-going, environmentally conscious locals. And if you’re an outdoorsy type, there are more than 275 parks and gardens within city limits, plus tons of hiking and biking trails.
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3. Montreal, Canada
- Flight Time from Chicago: 2 hours, 10 minutes
- Why We Recommend It: the museums, the architecture, the food and…did we mention the poutine?
- Where to Stay: Auberge de la Fontaine (from $167); Escad Hotel Quartier Dix30 (from $175); Hotel Uville Montreal (from $298)
Don’t have the time or budget to go to France? Jump on a flight, rock out to approximately two Celine Dion albums, and you’ll be in Montreal faster than you can say “incroyable.” While it’s delightfully low-key, there’s still tons of things to do in the largest city in Quebec. Don’t forget the Montreal Museum of Fine Arts, the breathtaking open-air market Marché Jean-Talon and of course, the poutine at La Banquise.
Iberostar Cozumel
4. Cozumel, Mexico
- Flight Time from Chicago: 3 hours, 50 minutes
- Why We Recommend It: off-the-beaten-path destination, swimming, scuba diving, snorkeling
- Where to Stay: Hotel B Cozumel (from $128); Allegro Cozumel (from $117); Iberostar Cozumel (from $158)
If the thought of waking up early to reserve a cabana at Montego Bay gives you hives (we get it), a trip to Cozumel may be more your style. This largely untouched Mexican island off the coast of the Yucatan Peninsula is an ocean adventurer’s dream, with sparkling turquoise water to snorkel, dive and swim in. If you’re looking to lounge on white sand, check out Dzul Ha, and if snorkeling is on your itinerary, head to the Palancar Reef for tropical fish and coral galore.
The Reykjavic Edition
5. Reykjavík, Iceland
- Flight Time from Chicago: 6 hours, 15 minutes
- Why We Recommend It: The Blue Lagoon, the Northern Lights, the local art and music scene
- Where to Stay: Iceland Parliament Hotel (from $265); Canopy by Hilton (from $295); The Reykjavik Edition (from $552)
This year, skip Aunt Judy’s Thanksgiving-dinner-slash-political-debate and hop a flight to Reykjavik. The Northern Lights will be the most visible around the holidays, and because it’s the off season, there will be fewer tourists. Plus, the Blue Lagoon is warm year-round, and much more picturesque with a little falling snow. OK, so while this flight isn’t super quick, you can still touch down just in time to eat a bowl of lobster soup at Saegreifinn, aka the Sea Baron, then grab a White Russian at the delightfully kitschy Lebowski Bar.
