Ready for a Labor Day Weekend Getaway from Chicago? This is the guide for you!
As a Midwest local, I’ve got you covered on tons of local (and far!) getaway ideas from Chicago over Labor Day weekend this year.
While there are plenty of amazing things to do over Labor Day weekend in Chicago, the long weekend provides you with the opportunity to explore outside of the city itself.
Whether you’re in the mood for a beach day on Lake Michigan, mountain hikes, or a vibrant city escape, this list includes something for every kind of traveler.
Labor Day Weekend Getaways From Chicago: Midwest
1. Indiana Dunes National Park
Just under an hour from Chicago, Indiana Dunes is a quick and easy escape for nature lovers.
The national park has some of my favorite Midwest hiking trails! You can get there by hopping in your car along major highways or taking a train from Chicago Union Station.
Spend the weekend hiking dune trails, relaxing on Lake Michigan beaches, or kayaking through wetlands.
The weather is usually warm and sunny over Labor Day, making it a perfect time for a final summer swim.
With plenty of picnic spots and scenic overlooks, it’s a low-key way to soak up the outdoors before fall arrives.
2. Starved Rock and Matthiessen State Park
If you’re looking to hike without traveling far, Starved Rock and Matthiessen State Park offer waterfalls, canyons, and forest trails just two hours from the city.
Both parks are ideal for a day trip or overnight stay, with rustic lodges and campsites available.
The first time I visited Starved Rock, I thought for sure I HAD to be out of the Midwest.
How in the world does flat Midwest have towering waterfall canyons and sandstone bluffs? Starved Rock is the answer.
Both state parks are also free to visit and park. I’m practically ready to drive over now. Who’s with me?
3. New Buffalo, Michigan
New Buffalo makes for a breezy beach town getaway under two hours from Chicago.
You can get there by car or a direct Amtrak train route from Chicago Union Station. The train conveniently drops you off directly in Downtown New Buffalo.
Spend the weekend swimming, browsing boutiques, or relaxing at local wineries.
It’s a great spot for couples or groups of friends who want to enjoy lake views, walkable downtowns, and easy access to Michigan’s Harbor Country.
Book early—Labor Day is a popular time to visit.
4. Holland, Saugatuck, and Douglas, Michigan
These neighboring towns along Lake Michigan are known for their charming streets, clean beaches, and artsy vibe.
I recommend combining a visit to multiple small towns along Lake Michigan, because why not?!
Of course this is up to your travel style, and you could easily plan yourself in just one of these towns and have a relaxing weekend.
Holland’s waterfront parks and tulip-lined paths feel peaceful this time of year.
Saugatuck and Douglas offer galleries, outdoor cafes, and scenic hikes at Saugatuck Dunes State Park.
It’s a slower-paced trip with beautiful lake views and a creative small-town feel.
5. Milwaukee, Wisconsin
Milwaukee is an underrated pick for a Labor Day escape. Honestly, it’s just an underrated city altogether!
The lakefront city blends cultural attractions with classic Midwest charm.
Grab a local brew at one of the city’s historic taverns, explore the Milwaukee Art Museum, or walk along the Riverwalk.
My favorite thing to do in Milwaukee is dine and hang out at Milwaukee Public Market, and stroll the Historic Third Ward after.
Labor Day weekend is a great time to visit Milwaukee because it often aligns with festivals and outdoor markets, and you’ll miss the massive summer crowds that hit during July’s Summerfest.
⭐Popular Milwaukee Tours
Labor Day Weekend Getaways From Chicago: USA
6. Denver, Colorado
Fly west for a long weekend in Denver, where you can enjoy mountain views and a lively downtown scene.
Denver is also an amazing base for outdoor adventures. Hike in the nearby Rockies during the day, then return for Denver’s craft breweries, street art, and food halls in the evening.
September usually brings cooler nights and golden aspen trees just starting to turn.
With direct flights from Chicago, it’s one of the most accessible Labor Day trips out west.
7. Miami, Florida
If you’re chasing sunshine, Miami delivers!
Spend your days on the beach, walking through the Art Deco District, or exploring colorful neighborhoods like Wynwood and Little Havana.
Little Havana is one of my favorite places to explore in Miami. I’m definitely signing up for a food tour on my next visit!
Labor Day weekend still feels like summer in Florida, but the vibe is more relaxed than peak winter tourist season.
Just prepare for heat and humidity—and don’t forget to start your mornings with a strong Cuban coffee.☕
8. Sedona, Arizona
I think Sedona is one of the most specatcularly beautiful places to visit in the United States!
And why not visit over Labor Day weekend when both the weather and crowds have cooled off?
Sedona is famous for its towering red rock formations at every turn.
Between hiking trails, grabbing dinner in town, or taking a beautiful drive, I don’t know which Sedona view is the most scenic.
Labor Day falls just before Arizona’s high season, so you can enjoy red rock hikes like Bell Rock and Cathedral Rock without big crowds.
In addition to hiking trails, there is a full range of activities besides hiking in Sedona!
The views are incredible, and the dry air makes even warm days feel manageable.
Add in a few art galleries or stargazing spots, and you’ve got a peaceful but scenic end-of-summer trip.
⭐Highly-Rated Sedona Hotels
⭐Popular Sedona Tours
9. Asheville, North Carolina
Asheville is a great pick for travelers who want cool mountain air, live music, and easy access to the outdoors.
Spend your mornings hiking in the Blue Ridge Mountains, then wind down with local beer and live music downtown.
Labor Day weekend often features small festivals and art walks, and the slightly cooler weather is perfect for sightseeing without the summer heat.
⭐Stay: Downtown Inn
10. Savannah, Georgia
Savannah is all about charm—cobblestone streets, oak trees draped in Spanish moss, and historic homes around every corner.
It’s slower-paced than other Southern cities, making it a good choice for travelers who want to explore on foot, try local cuisine, and enjoy warm early-September evenings.
Labor Day weekend gives you enough time to stroll, sip, and soak up the coastal Southern vibe without rushing.
Conclusion
Whether you’re hitting the road or hopping a flight, Labor Day weekend is the perfect excuse to squeeze in one last summer escape.
From Midwest parks and lake towns to mountain cities and beach getaways, these destinations offer something for every style of traveler.
Start planning early, pack light, and make the most of the long weekend from Chicago!
