Last Minute Trips for Chicagoans

Want to put off the harsh reality of work and school for a little bit longer? Then pack up the car and hit the road. No, you aren’t going to come across palm trees on any Midwestern adventure, but you will find blue skies, sandy beaches, delicious treats, and sites so beautiful you will actually look up from your phone to soak it all in. And the best part about my last trip suggestions is that the drive is under three hours and you can almost always find a great place to stay for the night–even if it is a spur of the moment decision. So where can Chicagoans go for last minute trips?

Sheboygan, Wisconsin

Distance from Chicago: 150 miles (2 1/2 hour drive)

Why it’s awesome: Get the best of both worlds…and indoor waterpark AND a beautiful Lake Michigan beach. Old fashioned ice cream parlors, mini golf, piers, lighthouses, tea time, world class spas and golf courses, and so much more await.

Where to stay with kids: Blue Harbor Resort

Where to stay when it’s just the two of you: American Club Resort

Galena, Illinois

Distance from Chicago: 165 miles (3 hour drive)

Why it’s awesome: The beautiful, rolling hills of Galena contain something for everyone. Race down Alpine slides, shop endless antique stores, taste the fruits of the local wineries, indulge in homemade fudge and treats, play a round of golf (including the mini version!), and brush up on your local history!

Where to stay with kids: Eagle Ridge Resort and Spa

Where to stay when it’s just the two of you: Galena Cellars

Lake Geneva, Wisconsin

Distance from Chicago: 85 miles (1 1/2 hour drive)

Why it’s awesome: Lake Geneva has absolutely everything you would want for a weekend of fun and relaxation. Beautiful beaches, parks, boat rides and rentals, mom and pop shops offering everything and anything under the sun, spas, golf courses, and delicious restaurants…the list goes on and on! And be sure to check out the Grand Geneva compound and all of the wet and wild fun it offers!

Where to stay with kids: Timber Ridge Lodge and Waterpark

Where to stay when it’s just the two of you: Grand Geneva Resort


Quad Cities, Illinois/Iowa

Distance from Chicago: 170 miles (2 1/2 hour drive)

Why it’s awesome: Take in beautiful Midwestern views along the mighty Mississippi when you travel between Rock Island, Moline, Davenport, and Bettendorf. Be sure to take a stroll along Augustana College’s beautiful campus, as well as climb onto tractors and trailers at the John Deere Pavilion. Don’t leave the area without enjoying a riverboat cruise…including the casino boats!

Where to stay with kids: Radisson on John Deere Commons-Moline

Where to stay when it’s just the two of you: Hotel Blackhawk

Looking for travel tips so your entire trip is a breeze from start to finish? I’ve got you covered!


Bon Voyage!
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  1. Julie says

    All 4 of these have been on our short list since we moved to Greater Chicago. Glad for the tips on where to stay when we finally do go… hopefully soon!

  2. Kathy says

    Last minute trips can be so much fun. That water park sure looks like a lot of fun. I know my kids would love to go to a water park again soon.

  3. Lynndee says

    We’ve never been to that part of the U.S. yet. We’ll, we’ve been to the Chicago O’Hare International Airport, but we’re definitely going to explore Chicago someday and hopefully, we get to visit those places that you’ve mentioned too. Btw, love that photo of the barn!

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