5 Things: A Travel Guide to Chicago



In “5 Things,” I’ll ask some of my favorite bloggers in cities all over the country to share insider travel tips on where to eat, shop, stay, and play in their neighborhoods (plus, what to pack to make the adventure complete). This week, Amanda Jane Jones shows us the sights in Chicago.

5 Things: Chicago Amanda Jane Jones

Graphic designer and art director Amanda Jane Jones lives in Chicago with her husband, Cree, and baby daughter, Jane. When she’s not working—she is one of the co-creators of Kinfolk Magazine and the designer of issues 1-13—Amanda can be found exploring the city she calls home, and documenting the details of her day-to-day on Instagram. She and her family love to explore Chicago’s restaurants and you can usually find them on a bike ride along Lake Michigan (weather permitting), or strolling around their sleepy neighborhood of Hyde Park. Today, she’s sharing some of her favorite places, spaces, and things to do…




Plein Air Cafe, 5751 South Woodlawn Avenue, (773) 966-7531

Big Star, 1531 North Damen Avenue, (773) 235-4039

Plein Air Cafe is right in our neighborhood and everything on the menu is delicious—we’ve tried it all! During the summers, we walk there for lunch every week. It’s one of our favorite Hyde Park haunts for sure. We also recommend Big Star, whose tacos we love so much, we’ll even drive through Friday night traffic to get them. The atmosphere there can be a bit loud, though, so we usually order takeout and eat it in the comfort of our home.



Independence, 47 East Oak Street, (312) 675-2105 

Independence, which features all American-made designs, has great menswear. It’s Cree’s favorite. And we always stop at Una Mae’s when we’re in Bucktown. They have really unique pieces that I can never find anywhere else. We both consider it a favorite.



AirBNB — Hyde Park or Bucktown Our favorite neighborhoods are Hyde Park—for the history and the beautiful architecture and Bucktown for the food. We love to eat out, so we’re usually up north at least once a week!








A few family-friendly recommendations:

Lincoln Park Zoo. Jane loves the polar bear, the sea lions, and the monkey house. Sometimes we drop in just to the see the monkeys and then head on our way. They even have a fun farm animals petting zoo that we like to visit when it’s warm. (Another plus: it’s free!)

The Children’s Museum at Navy Pier. We have a family pass here, and it’s the greatest thing. I highly recommend it. The Children’s Museum is just heaven for little kids: so many things to explore and touch and climb on. Jane always takes an excellent nap after we visit — she just wears herself out.

SkyDeck. The SkyDeck is a fun place to visit because it’s a great way to see the whole city. I’m always too nervous go out in the glass box, but I sure do love the view.

Garfield Park Conservatory. There are many conservatories in Chicago, but this one is our favorite. It’s really big and has a great slide that Jane loves. We like to visit in the winter, when we need a little warmth and a dose of nature in our lives.

Lake Michigan. The beach by our house is never very busy and sometimes we’re the only ones there — during the summer, we go almost every day. The lake shore trail goes all along the beach and up along the city. Family bike rides are a favorite activity of ours there, too.




Screen Shot 2015-02-02 at 2.16.52 PM

Chicago is really cold in the winter and chilly all the way to June. I’d pack lots of layers, and a good pair of boots if you’re coming in winter. If it’s summer, pack your swimsuit! The beach is right next to the city and the perfect cool-down. Jane and I go almost every day in the month of July.


Thank you so much, Amanda! (Thank you to Shoko Wanger for her help with this series.)

P.S. All entries in the 5 Things travel series. And our Chicago travelogue (one of the first ones on here).

Photos: Amanda Jane Jones, with exception—photos of Independence by Amy Jo Royall for Kinfolk.com.

Related posts:

Travel Guides

Browse By Category