7 May Airfares From Chicago You Simply Cannot Beat

$115 round-trip tickets, anyone?

By The Editors

7 May Airfares From Chicago You Simply Cannot Beat
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17 April 2018

Looking to get out of town? You’re in luck: May brings with its some terrific shoulder-season fares, whether you’re looking to keep it in the country (just over $100 to New York) or really get out of town (how’s Iceland for under $300 sound?). All fares double-checked for May flights and still available, at least at press time.


Photo: Flickr/Tiffany Von Armin

You’re Going To: Seattle, Washington

Roundtrip: $149 on Delta

Briefly: Between recreational marijuana and the elephantine shadows of Mt. Rainier, Seattle’s natural bounty is everywhere. However, leave the umbrella at home and buy yourself a proper rain jacket, as the locals do.

Stay At: The Thompson Seattle, which is walking distance from the Seattle Art Museum and Pike Place Market. Pro tip: get a room with views of Puget Sound.

Stop By: Olympic Sculpture Park, the Amazon Spheres, Filson’s Seattle Flagship, Ebbets Field Flannels and JuneBaby, which is being billed by many as America’s next great Southern restaurant.


Public Hotel

You’re Going To: New York City, New York

Roundtrip: $116 on Spirit

Briefly: Ah, New York. Still a thing. And it will always be a thing if airfares stay this low for the less-than-two-hour flight out east.

Stay At: The new Public Hotel in Manhattan’s Lower East Side — maybe steer clear of the Jean-Georges-helmed Public Kitchen.

Stop By: The Dream Machine pop-up (your Instagram demands it), Olmstead, “David Bowie Is” at the Brooklyn Museum and The Met Cloisters.

You’re Going To: Montreal, Canada

Roundtrip: $245 on Porter Airlines

Briefly: Like a European vacation without crossing the Atlantic. Plus: eating. Oh, how there will be eating.

Stay At: The spiffy new Hotel Monville, where robots are at your beck and call

Stop By: Canadian Center for Architecture, Montreal Museum of Fine Arts, Lester’s Deli (or Schwartz's) and Arthur’s Nosh Bar.


Catahoula Hotel

You’re Going To: New Orleans, Louisiana 

Roundtrip: $138 on United

Briefly: New Orleans turns 300 this year, making it the perfect time to go and discover (or remind yourself) why The Big Easy is a world-class city.

Stay At: Catahoula Hotel, located in a masterfully rehabbed 1845 Creole townhouse and a stone’s throw away from Jackson Square, in the heart of the French Quarter.

Stop By: Preservation Hall, Faulkner House Books, Compère Lapin and Turkey and the Wolf.


Photo: Eli Noto

You’re Going To: Reykavik, Iceland

Roundtrip: $260 on Wow Air

Briefly: Everyone you know has been there, but it’s still great — especially if you do it better by renting a 4x4 with a tow-along teardrop trailer.

Stay At: A Mink Camper if you wanna do Ring Road properly, but also the just-opened Retreat at the Blue Lagoon if you want to kill two birds with one stone.

Stop By: The Secret Lagoon, Thrinukagigur volcano, Fontana Natural Steam Bath and Apotek.

You’re Going To: San Juan, Puerto Rico

Roundtrip: $230 on Delta

Briefly: The truth is the Caribbean is still suffering from Hurricane Irma and Maria, but tourism is one of the speediest, most steadfast paths to recovery.

Stay At: The 12-room oceanfront hotel The Dreamcatcher, especially for the option to volunteer in recovery efforts, or the newly (and miraculously) opened Serefina Hotel.

Stop By: Luca, La Factoria, JungleBird.


Palacio de Bellas Artes

You’re Going To: Mexico City, Mexico

Roundtrip: $270 on InterJet

Briefly: Edgy, creative and tacos al pastor. Is that Mexico City in a nutshell? Definitely not. But that’s enough reasons for you to go, stat.

Stay At: La Valise, with just three suites, located inside an early 20th-century French-inspired building. Don’t sleep on the city’s plethora of incredible Airbnb stays, either.

Stop By: Frida Kahlo Museum, Museo del Juguete Antiguo,  Casa Gilardi, Rosetta Restaurante and La Mercad Market.

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