10 Best Weekend Getaways from Naperville, Illinois (within a 4-hour flight)
- Jordan Hinsch
- 7 days ago
- 5 min read
Naperville, Illinois, is a vibrant city in the Chicago metropolitan area known for its excellent schools, thriving business scene, and family-friendly atmosphere. It features a charming downtown, scenic Riverwalk, and numerous parks, making it one of the best places to live in the U.S.
If you're a local and looking to escape for a weekend, keep reading. With a vast array of short domestic destinations, there are also some international destinations within reach. Here are some weekend getaway ideas for locals in the Naperville, Illinois, 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) - 2.5 Hour Flight
Why go?
Beaches, outdoors activities, clubs, restaurants, culture. I just ask that you please please please venture out beyond Miami Beach.
What to do?
Click here to view The BEST Things to Do in Miami
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
How much will it cost to get there?
Airfare: $100+
Where can you stay?
Who will pick you up?
Pro Tip:
Visit the following neighborhoods to step away from the "typical Miami": Wynwood, Brickell, Coral Gables, Coconut Grove, Midtown, Edgewater.
New York, New York (JFK, LGA, EWR, ISP, HPN) - 2 Hour Flight
Why go?
It might not be the same city it was before, but it'll always make for a great weekend getaway.
What to do?
Click here to view The BEST Things to Do in New York
When to go?
Summer for the best weather, but you’ll pay peak rates for solid hotels.
Winter for Christmas festivities!
Who can fly you there?
AA from ORD - See flight deals
How much will it cost to get there?
Airfare: $100+
Where can you stay?
Who will pick you up?
Las Vegas, Nevada (LAS) - 4 Hour Flight
Why go?
Gambling, Hoover Dam, Death Valley National Park, Valley of Fire State Park, Partying, more Gambling.
What to do?
Click here to view The BEST Things to Do in Las Vegas
When to go?
Year-Round
Who can fly you there?
Southwest from MDW - See flight deals
How much will it cost to get there?
Airfare: $90+
Where can you stay?
Who will pick you up?
Denver, Colorado (DEN) - 2 Hour 50 Minute Flight
Why go?
Mountains, beer, National Parks, hiking, clean city, nice people.
What to do?
Click here to view The BEST Things to Do in Denver
When to go?
Year-round. Ski in the winter. Hike in the summer.
Who can fly you there?
United from ORD - See flight deals
Frontier from MDW - See flight deals
Frontier from ORD - See flight deals
How much will it cost to get there?
Airfare: $39+
Where can you stay?
Who will pick you up?
Austin, Texas (AUS) - 2 Hour 52 Minute Flight
Why go?
Food, Art, Music, BBQ, Tech, Bach Parties, and All-Around Fun!
What to do?
Click here to view The BEST Things to Do in Austin
When to go?
Year-Round
Who can fly you there?
American from ORD - See flight deals
Frontier from ORD - See flight deals
How much will it cost to get there?
Airfare: $44+
Where can you stay?
Who will pick you up?
Calgary, Alberta (YYC) - 3 Hour 52 Minute Flight
Why go?
Calgary is a vibrant city that serves as a gateway to the majestic Rocky Mountains, offering a dynamic mix of modern attractions, rich cultural festivals, and immediate access to outdoor adventures.
What to do?
Click here to view The BEST Things to Do in Calgary
When to go?
Summer
Who can fly you there?
American from ORD - See flight deals
United from ORD - See flight deals
How much will it cost to get there?
Airfare: $96+
Where can you stay?
Who will pick you up?
Salt Lake City, Utah (SLC) - 3 Hour 35 Minute Flight
Why go?
Skiing, Salt Flats, Mormons, and great National Parks within a moderate drive.
What to do?
Click here to view The BEST Things to Do in Salt Lake City
When to go?
Year-Round
Who can fly you there?
Frontier from ORD - See flight deals
American from ORD - See flight deals
United from ORD - See flight deals
How much will it cost to get there?
Airfare: $49+
Where can you stay?
Who will pick you up?
Aspen, Colorado (ASE) - 3 Hour 13 Minute Flight
Why go?
Skiing, great scenery, luxury.
What to do?
Click here to view The BEST Things to Do in Aspen
When to go?
Year-round
Who can fly you there?
United from ORD - See flight deals
American from ORD - See flight deals
How much will it cost to get there?
Airfare: $285+
Where can you stay?
Who will pick you up?
Pro Tip:
It's very expensive, but worth a shot. 3.5 hour drive from Denver if you wish to save some $$.
Jackson Hole, Wyoming (JAC) - 3 Hour 18 Minute Flight
Why go?
Bears, Yellowstone National Park, Grand Teton National Park, skiing, golfing, horseback riding, rustic boutique hotels, cool people.
What to do?
Click here to view The BEST Things to Do in Jackson Hole
When to go?
Year-round
Who can fly you there?
United from ORD - See flight deals
American from ORD - See flight deals
How much will it cost to get there?
Airfare: $231+
Where can you stay?
Who will pick you up?
Pro Tip:
Make sure you have time to visit both Yellowstone and Grand Teton. Jenny Lake is a must.
Bozeman, Montana (BZN) - 3 Hour 10 Minute 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.
What to do?
Click here to view The BEST Things to Do in Bozeman
When to go?
Year-Round
Who can fly you there?
Southwest from MDW - See flight deals
American from ORD - See flight deals
How much will it cost to get there?
Airfare: $185+
Where can you stay?
Who will pick you up?
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