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  • Writer's pictureJordan Hinsch

26 Best Weekend Getaways from Chicago (within a 4-hour flight)

Updated: Jan 21



Deep dish pizza, sports, great bars, and awesome summers. Chicago has it all (except the ocean and nice winters). If you're looking to take a break from the norm in Chicago or escape the brutal winter, read on for some ideas about where to go for a quick weekend.


With a vast array of short domestic destinations, there are also many international destinations within reach. Here are some weekend getaway ideas for locals in the Chicago area within a non-stop 4-hour flight. More importantly, these trips are all possible without having to request PTO (for you M-F 9-5'ers), it just depends on what you want to do at your destination.





Miami, Florida (MIA, FLL) - Just Over a 3 Hour Flight


Why go?

  • Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.

When to go?

  • Any time of the year, but best is October - February for perfect weather. Avoid the spring break crowd in late Feb/early March the best you can.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?

Pro Tip:

  • Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.




Orlando, Florida (MCO) - Just Under a 3 Hour Flight


Why go?

  • Disney & Universal Studios. Bring bug spray and an umbrella if you go during the summer.

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $150+

Where can you stay?








New York, New York (JFK, LGA, EWR, ISP, HPN) - 2 Hour Flight


Why go?

  • It might not be the same city it was a few years ago, but it'll always make for a great weekend getaway.

When to go?

  • Summer for the best weather, but peak rates for solid hotels.

  • Winter for Christmas festivities!

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?







Toronto, Ontario (YYZ, YTZ) - Just Under a 2 Hour Flight


Why go?

  • Food, people, cleanliness, Hockey Hall of Fame.

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?



Philadelphia, Pennsylvania (PHL) - 2 Hour Flight


Why go?

  • History, sports, cheesesteaks

When to go?

  • Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?





Washington, DC (IAD, DCA, BWI) - Just Under a 2 Hour Flight


Why go?

  • Museums, walking tours, great mass-transit and cherry blossoms. Fly to DCA for convenience.

When to go?

  • Year-round (spring season for cherry blossoms)

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?

Pro Tip:

  • For avid runners, pack your running shoes and go for daily runs around the White House, Washington Monument, Lincoln and Jefferson memorials.

  • Discover the ease of weekend escapes from Chicago with ING Chauffeured Transportation, your trusted choice for dependable ground transportation.



Kansas City, Missouri (MCI) - 1.5 Hour Flight


Why go?

  • BBQ! BBQ! BBQ!

When to go?

  • Year-round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $150+

Where can you stay?

Pro Tip:

  • Visit the Power & Light District for a unique nightlife experience & go to Arthur Bryant's for BBQ.




Nashville, Tennessee (BNA) - 1.5 Hour Flight


Why go?

  • Music (not just country), endless bars, brewpubs, hot chicken.

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?

Pro Tip:

  • Stay in the Gulch or near printer's alley.





New Orleans, Louisiana (MSY) - 2.5 Hour Flight


Why go?

  • Jazz music, other music, culture, architecture, partying, passionate football fans.

When to go?

  • Spring, Summer, Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $50+

Where can you stay?

Pro Tip:

  • Check out Bourbon Street for a little bit, but don't get sucked in. It's absolutely disgusting. Chartres Street is better for those looking to maintain their cleanliness.




Atlanta, Georgia (ATL) - 2 Hour Flight


Why go?

  • Brew pubs, art, nightlife, Mexican food.

When to go?

  • Year-round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?

Pro Tip:

  • Walk some of the BeltLine and stop at stores, bars, and restaurants.



Raleigh, North Carolina (RDU) - 2 Hour Flight


Why go?

  • Outdoors activities, restaurants, college sports, booming tech sector.

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?



Glacier National Park, Montana (FCA) - Just Over a 4 Hour Flight


Why go?

  • Glacier National Park and the great town of Whitefish. I recommend camping, but you can get a boutique hotel in Whitefish or Kalispell.

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $350+

Where can you stay?



Austin, Texas (AUS) - Just Under a 3 Hour Flight


Why go?

  • Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?




Cancun, Mexico (CUN) - Just Under a 4 Hour Flight


Why go?

  • Your money goes a long way: all-inclusive hotels, nightlife, and activities.

When to go?

  • December to April for the best weather.

  • Avoid March Spring Break travel if you want to be at peace.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?



Jackson Hole, Wyoming (JAC) - Just Over a 3 Hour Flight


Why go?

  • Bears, Yellowstone National Park, Grand Teton National Park, skiing, golfing, horseback riding, rustic boutique hotels, cool people.

When to go?

  • Year-round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $400+

Where can you stay?

Pro Tip:

  • Make sure you have time to visit both Yellowstone and Grand Teton. Jenny Lake is a must.



Aspen, Colorado (ASE) - Just Over a 3 Hour Flight


Why go?

  • Skiing, great scenery, luxury.

When to go?

  • Year-round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $400+

Where can you stay?

Pro Tip:

  • It's very expensive, but worth a shot. 3.5 hour drive if you wish to save some $$.




Boston, Massachusetts (BOS) - Just Over a 2 Hour Flight


Why go?

  • History and cool summertime temps!

When to go?

  • Summer for the best weather, but peak rates for solid hotels.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $100+

Where can you stay?



Las Vegas, Nevada (LAS) - 4 Hour Flight


Why go?

  • Gambling, Hoover Dam, Death Valley National Park, Valley of Fire State Park, Partying, more Gambling.

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $150+

Where can you stay?



Denver, Colorado (DEN) - Just Under a 3 Hour Flight


Why go?

  • Mountains, beer, National Parks, hiking, clean city, nice people.

When to go?

  • Year-round. Ski in the winter. Hike in the summer.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $250+

Where can you stay?




Salt Lake City, Utah (SLC) - 3.5 Hour Flight


Why go?

  • Skiing, Salt Flats, Mormons, and great National Parks within a moderate drive.

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $350+

Where can you stay?



Nassau, Bahamas (NAS) - 3.5 Hour Flight


Why go?

  • Turquoise waters, friendly people, and close proximity to Florida make the Bahamas a popular destination.

When to go?

  • December to July to avoid hurricanes and tropical storms.

  • May to August to avoid crowds and surcharges.

  • November to February to avoid the summer heat.

Who can fly you there?

How much will it cost to get there?

  • Airfare: $500+

Where can you stay?

Pro Tip:

  • Rent a car! Be prepared to drive on the left side of the road.





Charleston, South Carolina (CHS) - 2 Hour Flight


Why go?

  • History, culture, family-friendly attractions, and watersports.

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?



Asheville, North Carolina (AVL) - Just Under a 2 Hour Flight


Why go?

  • Art, craft beer, and the Smoky Mountains. I'd recommend driving instead of flying, but it's your call!

When to go?

  • Spring, Summer and Fall

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?



Montreal, Quebec (YUL) - 2 Hour Flight


Why go?

  • More restaurants per capita than any other North American city.

When to go?

  • Summer

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?



Bozeman, Montana (BZN) - 3.5 Hour Flight



Why go?

  • Skiing, Hiking, Waterfalls, Museums, Rivers, and of course Yellowstone National Park (1.5-hour drive). It's possible to do the park in one day from Bozeman, but if going to the park is your goal, I'd recommend staying closer to the park in West Yellowstone.

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $400+

Where can you stay?



Rapid City, South Dakota (RAP) - 2.5 Hour Flight



Why go?

  • You'll find nature and parks galore in one of the most unique areas of the country. Mt. Rushmore National Monument, Custer State Park, Black Hills National Forest -- all within a 35 min drive from Rapid City, in the same direction. Do all 3 in one day and be sure to visit Sylvan Lake in Custer. Just incredible. Badlands National Park is 1 hour away and that's doable in a separate day. Devils Tower National Monument is just under 2 hours in the opposite direction across the Wyoming border.

When to go?

  • Year-Round

Who can fly you there?

How much will it cost to get there?

  • Airfare: $200+

Where can you stay?




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Hey! I'm Jordan, a native New Yorker who is addicted to adventure travel, photography, content creation, investing, and fitness. Read on, enjoy, and Never Run Out of First Times!

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