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  • Jordan Hinsch

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



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.


Bear in Mind: When traveling internationally, you may be required to show proof of a negative Covid-19 test or proof of vaccination. Check relevant embassy websites for the most up to date information.



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?