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Weekend getaways from Chicago

From far-flung adventures to family trips, here's everything you need to plan your weekend getaways from Chicago

Photograph: Indiana Dunes National Park
Indiana Dunes National Park

Weekend getaways from Chicago are our reward for making it through week after week with hardly any complaining. While we can't always hop on a plane to Maui or even make the shorter escape to Philadelphia, we can almost always find time for a weekend away. Chicago's central location means we're just a day's drive from exploring new farmers markets, craft beer destinations and other great spots for finding regional foods. Whether you're looking for a long weekend spent hitting restaurants and bars, a relaxing staycation or a kid-friendly getaway, we've got you covered with itineraries for making the most of your adventure.

Weekend getaway ideas from Chicago

Travel to Madison, Wisconsin
Travel

Travel to Madison, Wisconsin

Prepare for hundreds of bicycles and plenty of chances to laze by the water or kick back with a beer

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Travel to Austin, Texas
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Travel to Austin, Texas

A trip to Austin should satisfy your cravings for authentic BBQ and country bars

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Travel to Milwaukee
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Travel to Milwaukee

Wisconsin’s largest city is another epicenter of art and food set on Lake Michigan

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Travel to Holland, Michigan
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Travel to Holland, Michigan

You don’t have to travel over the ocean to explore Dutch history

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Travel to Grand Rapids
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Travel to Grand Rapids

If you love craft beer, you’ll love Grand Rapids

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Travel to Harbor Country, Michigan
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Travel to Harbor Country, Michigan

These small cities on the water feel like every bit of an old resort 

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The best Midwest summer music festivals
Music

The best Midwest summer music festivals

Hear that? That's the sound of a rockin' road trip. 

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14 unexpected great vacations from Chicago
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14 unexpected great vacations from Chicago

Consider these direct flights from O'Hare for mountains, water and swathes of green space

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Day trips from Chicago
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Day trips from Chicago

Chicago is the perfect launchpad for a host of one-day escapes

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Family-friendly day trips from Chicago
Kids

Family-friendly day trips from Chicago

These family-friendly day trips will get the kids out on the road sans the "Are we there yet?" soundtrack

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Chicago staycation ideas

The best Chicago staycation ideas
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The best Chicago staycation ideas

High-rise hotels, bed-and-breakfasts and even tiny, chic boutique rooms await

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The 9 coolest Airbnb rentals in Chicago
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The 9 coolest Airbnb rentals in Chicago

Chicago has some truly amazing Airbnb options

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The best downtown Chicago hotels in the Loop
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The best downtown Chicago hotels in the Loop

Where to stay in the heart of the city

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Your perfect weekend: Andersonville
Things to do

Your perfect weekend: Andersonville

Andersonville is easily one of Chicago's best neighborhoods

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Food adventures from Chicago

Where to eat in Door County, WI
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Where to eat in Door County, WI

The region mixes tradition with contemporary flavors

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What to eat and drink in Louisville, KY
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What to eat and drink in Louisville, KY

Tiki, tacos and a lot more than bourbon await

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What to order in Minneapolis & St. Paul, MN
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What to order in Minneapolis & St. Paul, MN

The Twin Cities blend hyperlocal ingredients with global influences

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Where to eat and drink in St. Louis, MO
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Where to eat and drink in St. Louis, MO

There's far more to the Gateway City than barbecue

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Where to eat in Indianapolis, IN
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Where to eat in Indianapolis, IN

The underrated food city deserves a fresh look

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Where to eat in Cleveland, OH
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Where to eat in Cleveland, OH

The Ohio city is an up-and-coming culinary destination

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Where to eat in Harbor Country, MI
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Where to eat in Harbor Country, MI

Here's where to eat on your Michigan weekend getaway

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Explore even more in Milwaukee
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Explore even more in Milwaukee

Local experts help us craft the insider’s guide

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