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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?
AA from ORD - See flight deals
Spirit Airways from ORD - See flight deals
Southwest from ORD, MDW - See flight deals
United from ORD - See flight deals
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?
AA from ORD - See flight deals
Spirit Airways from ORD - See flight deals
Frontier from ORD - See flight deals
Southwest from ORD, MDW - See flight deals
United from ORD - See flight deals
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?
AA from ORD - See flight deals
Delta from ORD - See flight deals
United from ORD - See flight deals
Spirit Airways from ORD - See flight deals
JetBlue from ORD - See flight deals
Southwest from ORD, MDW - See flight deals
How much will it cost to get there?
Airfare: $50+
Where can you stay?