Road Trip Ideas from Chicago for You and Bae

road trip with bae ideas

There’s nothing to do and nowhere to go. Dating right now can be a bit challenging, but it can also bring you closer. So, I wanted to share how you can pick a place to go on a road trip with your boyfriend from Chicago. Hopefully, it will be easier for you to plan a nice road trip with bae.

I will preface this by saying this was our first road trip together. So, there was some anxiety around it like how far of a road trip is too far, are we good drivers, and what do we do in the car, etc.

cities near Chicago:

Ahh the questions – what are your road trip options from Chicago? We both have been in Chicago for awhile. And I’ve gone on a lot of weekend aways. So, I just want to put that out there. We wanted to go somewhere that neither of us has been. With that said, Saint Louis, Milwaukee, Detroit, Ann Arbor, Grand Rapids, Cincinnati, Indianapolis, Traverse City, Green Bay – are all great places that one of us had been to.

Well, to start, I thought let’s do something that might be plausible – like renting a cabin for the weekend and being in nature. That was cute and all until we realized that cabins on AirBnB had no plumbing ( I wish I was joking – everyone has booked a cabin and all that was left were these) and that’s not romantic. And when we looked at Bed & Breakfasts we realized the four-post beds and flower wallpaper was not our style.

We had a breaking point when looking at cabins – seriously they are going fast. And we just couldn’t look at wood on wood anymore.

I’m gonna be honest with you, there are not that many cities within driving distance of Chicago. There’s also not a big change of scenery – we don’t have mountains or hills nearby. Lake Michigan is nice, but it’s not really an attraction until the summer since it’s so cold.

We started out by going on YouTube and looking at cities by us and taking virtual tours. When we got to Iowa City, we knew that the places we were going to were all going to be less exciting than Chicago – since Chicago is arguably the best city in America. So, this helped us set our expectations – it might not wow us, but we could enjoy a new place.


  1. Do Virtual City Tours – the drone shots of cities are so cool, but also there are driving tours and YouTubers spending a weekend in the city. A couple doing a food tour in Madison, WI made us excited about the food there. We also saw a surprise proposal at Hocking Hills State Park. It was nice to get a feel for a place before we went.
    1. Columbus
    2. Cleveland
    3. Minneapolis
    4. Iowa City
    5. Madison
    6. Nashville
  2. Look at shows for inspiration – what better way to get ideas for road trips with bae than through shows! We’ve been watching Marriage or Mortgage, which is set in Nashville, TN. It made us really want to go there. And, Say I Do is set in Cincinnati. It’s nice that new Netflix shows are set in the Midwest and other cities besides LA and NY.
  3. Go to Google Maps and look at distance. This was a crucial part of our decision-making. For 2 days away, and a rest day, we didn’t want to drive more than 5 hours each way.
  4. Go beyond AirBnB. Finding a cool place to stay is part of the fun of going away – since we’ve all been in our house too long. Finding a place you can relax and enjoy the ambiance, I think, is a big part of going anywhere.
  5. Check out activities that are open before you go. In Madison, WI, for instance, we found two art museums and noticed you needed to reserve a time for one of them before we went – since the museum was limited. Also, at state parks, bathrooms can be closed – which can be very unpleasant if you’re staying hydrated and need to pee.

Road Trip with Bae Options:

Option 1: Go to Starved Rock and rent a cool AirBnB

Option 2: Go to a city and a state park nearby (i.e. Columbus and Hocking Hills State Park)

Option 3: Find a cabin (really wanted a hot tub in the woods vibe)

Option 4: Take a longer drive to a city and skip nature (Minneapolis or Nashville)

Option 5: Camping

road trip with bae ideas from chicago
Photo: Glass house Candlewood Cabins in Wisconsin

We decided that going to Starved Rock was just a day trip, which if you’re looking for day trip ideas, here’s a list of Chicago day trips from The Quirky Travel Guy. There was no reason to make a weekend out of it because there’s nothing cool nearby. It’s still on our list to go. When we saw YouTube videos, people were saying how crowded it was and how people were littering. So, it made it less appealing to just go there. also, don’t liter.

We really liked the idea of going to a city and a state park. The only thing was that the drive would be the same as going to a cool city like Nashville. And we would both rather be in Nashville than Ohio. But, we had both been to Nashville.

When we looked at the prices of resorts, we thought that we would rather be on an island or beach somewhere rather than a cabin in Indiana or Missouri. (I cringe as I type that, but cabin resorts have sweet amenities ).

As for camping, we wanted a little something more than roughing it for our first road trip.

Nature + City Weekend Away:

To make the most of our weekend, we decided that finding a state park near a city would be best.

We had two options: Madison, WI and Devils Lake or Columbus, and Hocking Hills State Park. Madison, WI is just over a 2-hour drive, so you feel like you’re getting away without going too far. And the state park was an hour away. For Columbus, OH, it was about 5.5 hours to drive there and about another hour to the state park. We thought that spending the day at a park and driving back almost 7 hours would be kind of brutal.

Road Trip with Bae – Where we went:

We spent the weekend in Madison, WI. It was wonderful. We climbed arguably, 500 ft. At Devil’s Lake, made friends, enjoyed beer, and stayed in a trendy hotel where we met people from Minneapolis, who told me that I made the right decision going to Madison, WI and Devil’s Lake State Park. I’m glad that I virtually explored the Midwest more and got to hike.

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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