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Top 5 Getaway Towns Outside of Chicago

Top 5 Getaway Towns Outside of Chicago

Top 5 Getaway Towns Outside of Chicago

To me Chicago is one of the most beautiful metropolitan cities in the country.  It has everything you could possibly need; the best restaurants, beautiful beaches, amazing museums and friendly faces.  There’s a pulse to the city unlike any I’ve ever been to before with a since of urgency and hustle and bustle, while still remaining friendly and humble.  And while we can retreat to our wonderful city neighborhoods to avoid some of the downtown crowds, sometimes you truly need a break from it all.  And I get it! As one of Chicago’s biggest supporters, I too enjoy traveling outside of the city every now and then. 

The beauty of being in the Midwest is that we are literally in the smack dab middle of a ton of action.  Growing up in the Southwest, for me the nearest cities were a good four or five hours drive away, but here you can take a short trip up to Wisconsin in less than two hours!! There are so many places I’ve yet to go and trips I want to make, but here are my favorite places I’ve visited outside of the city so far.

Milwaukee, WI (102 miles N of Chicago)

Almost seems like an obvious choice, but the reality is the drive to Milwaukee is basically equivalent to a traffic-infused drive to the suburbs.  You can get to Milwaukee in about 90 minutes by car or train.  While Milwaukee is still has more of city vibe than scenic outdoorsy feel (it’s the fifth-largest city in the Midwest), it’s definitely a lot smaller and slowed down than the Chicago we know and love.  The beauty of Milwaukee being as what I think of as a “smaller version of Chicago,” there’s still a lot of fun things to do and places to visit. 

The Milwaukee Art Museum is one of the most-notable attractions in the Milwaukee area.  The building itself is a work of art with the addition of the museum’s “wings” designed by Spanish architect Santiago Calatrava; the addition was completed in 2001.  The art museum has over 30,000 works of art and continues to grow into one of the country’s largest art museums. 

You can take a tour of the Pabst Mansion. Milwaukee is well known for its selection of beers.  You can visit the king of PBR Captain Frederick Pabst’s family home, but this is no beer tour.  Just a tour of a beautiful restored home that’s an important part of Milwaukee’s history.  Similar to Chicago, Milwaukee also has a lot of beautiful beaches and lakefront paths overlooking the always-stunning Lake Michigan. 

Starved Rock State Park (93 miles SW of Chicago)

Depending on traffic you can arrive in a beautiful state park in less than two hours.  What is so beautiful about Starved Rock is that it’s not very far of a drive, but once you arrive it feels like you’re completely surrounded by nature.  There are streams, waterfalls and trails galore that could entertain you for days.  Starved Rock is a great daytrip, but you can easily extend the trip to a weekend by renting a room at their lodge, camping or staying at a neighboring town.  With multiple waterfalls in 14 of the 18 canyons, they’re breathtakingly beautiful and can be explored during every season.  Although it may get chilly in the winter, a frozen waterfall is an incredible sight to be seen.

Madison, WI (About 147 miles NW of Chicago)

When I think of the epitome of a college drinking town, I think of Madison, Wisconsin.  The capital of the cheese state is probably best known as the home to the University of Wisconsin-Madison, where students live, learn and give back to their surrounding community.  Much like Milwaukee, Madison offers that small town version of a big city.  With plenty of shopping and bike trails, it’s one of the most “bikeable” cities in the country. 

You can see and tour the beautiful State Capital building and picnic by Lake Mendota or Lake Waubesa.  Explore the beautiful gardens at Olbrich Botanical Gardens or visit the Madison Museum of Contemporary Art.  Much like Milwaukee, Madison gives you all the things you love about Chicago, but with fewer crowds. 

Galena, IL (About 164 miles W of Chicago)

Nearly four hours outside of the third most-populous city in the country (Chicago) is the most adorable town called, Galena.  Galena is known as the “wine country of the Midwest” and has multiple vineyards, tours and shopping areas.  They also host an annual hot air balloon race that brings in crowds from all over the country.  Enjoy the best Galena has to offer by visiting one of their local vineyards.  Check out Galena Cellars Vineyard for wine tastings and a great selection of wines.  If you’re interested in something a little weirder, you can take a ghost tour at Amelia’s Galina’s Ghost Tours for a haunting tour.  And don’t pass up the opportunity to visit the Galena Territories.  Awe-inducing views surround you if you take a drive through the beautiful scenery.  The rolling hills remind me of The Sound of Music, incredibly stunning.  There’s a little something for everyone in this adorable town with plenty of nature and local shopping for all.

Dubuque, IA (About 180 miles NW of Chicago)

If you drive just a few miles further NW past Galena, you’ll come across one of the quaintest towns I’ve ever seen, Dubuque, Iowa. Dubuque is positioned within just a few miles of Iowa, Illinois and Wisconsin borders.  The Mines of Spain was one of the most beautiful state parks I’d ever seen.  It reminded me a little of the southwest and I loved every minute of it.  The best advice I can give, however, is don’t forget the bug spray! I got eaten alive on my trip there, but the beauty of it all was worth it.  Eagle Point Park is another beautiful point of interest.  From high up you can overlook the town along the Mississippi River.  A spectacular vantage point and for only $1 you have access to the park with the option to return once more for the day for free.  Warning, no pets allowed here! My other favorite stop in Dubuque was the beautiful Dubuque Arboretum & Botanical Gardens.  The amazing free space was such a nice way to end the day.  With tons of gardens and beautiful photo opportunities, this spot is well worth the visit.  Aside from the gardens and parks, you can stroll along the Mississippi river or grab some dinner downtown.  Overall Dubuque is a wonderful town that has so many beautiful sights to see. 

So you see! There’s so much to do and see outside of Chicago.  If you’re up for it you can make even longer drives closer to five hours and see even more amazing towns and cities this great country has to offer.  Next on my bucket list is a visit to Toronto! So get out there and explore! The only limit is your imagination!

Points of Interest:

Milwaukee Art Museum
700 N Art Museum Dr.
Milwaukee, WI 53202

Pabst Mansion
2000 W Wisconsin Ave.
Milwaukee, WI 53233

Starved Rock State Park
2668 East 873 Rd.
Oglesby, IL 61348

State Capital building
2 E Main St.
Madison, WI 53703

Olbrich Botanical Gardens
3330 Atwood Ave.
Madison, WI 53704

Madison Museum of Contemporary Art
227 State St.
Madison, WI 53703

Galena Cellars Vineyard
4746 N Ford Rd.
Galena, IL 61036

Amelia’s Galina’s Ghost Tours
303 S Main St.
Galena, IL 61036

The Galena Territory
Guilford Township, IL 61036

Mines of Spain
8991 Bellevue Hts.
Dubuque, IA 52003

Eagle Point Park
Eagle Point Dr.
Dubuque, IA 52004

Dubuque Arboretum & Botanical Gardens
3800 Arboretum Dr.
Dubuque, IA 52001