Travel Bug: Touring Chicago with Blonde Bedhead

After traveling to the South and the Southern Hemisphere, we felt it was time to travel northward and visit Chicago style blogger Andrea of Blonde Bedhead. Plan your next trip to the Windy City with Andrea’s guide in hand, because after hitting up all the tourist sites, you’ll want to fill the remainder of your hours with top-notch food and fashion.

“With so many neighborhoods and places to visit in Chicago, it can seem overwhelming, but for the girl who enjoys a quaint, delicious breakfast, great shopping in low-key areas and thinks planning a trip around an amazing vintage expo would be the perfect trip, this should be your guide,” says Andrea.

Our tour guide sports the No Shatter What Dress and Betsey Johnson Bright Said Red Boot.

1. Milk & Honey. “Milk & Honey is a quaint café located in the Bucktown neighborhood. With outdoor seating, it’s the perfect place to go early on a summer morning before the brunch rush, or, sit inside to watch the snow during the winter through its large windows. The breakfast panini and waffles are my favorite items on the chalkboard menu. Oh, and the cute hipster waiters are easy on the eyes too.”

2. Molly’s Cupcakes. “If you’re in search of the most delectable baked good in a fun atmosphere, Molly’s Cupcakes in Lincoln Park has the best cupcakes in all the land. Particularly their stuffed cupcakes filled with everything from cake
batter to cookie dough. Go with a small group, play a couple board games and try to snag a swing at the bar. Yep, there are swings to bring out your inner child!”

3. Comfort Me. “After you’re done grabbing a cupcake from Molly’s, head down the street to Comfort Me, a boutique located in Lincoln Park. The vintage jewelry and great selection of denim jeans are a couple of my favorite items that draw me in. The shop is like a ray of sunshine and I always leave in a better mood than I came in.”

4. Pilsen. “The Pilsen neighborhood boasts some great vintage shops with Knee Deep Vintage and Pilsen Vintage and Thrift topping my list. Knee Deep Vintage boasts a large selection of men’s and women’s clothing with a focus on ’20s – ’50s. Pilsen Vintage and Thrift has a smaller selection of clothing, but has a variety of accessories and fun pieces for the home.”

5. The Modern Vintage Expo. “The Modern Vintage Expo is a fabulous enough event to plan an entire trip to Chicago around. The Randolph Street Market hosts a variety of vintage events year-round, but this huge event focusing on fashion and accessories is by far my favorite. The expo brings vendors from across the country with great vintage fur finds, beautiful jewelry, and just a great selection of clothing spanning all eras.”

Thanks for the tour, Andrea! For those of you who’ve been to the Windy City, what would you add to the list?

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  1. Hannah (ModCloth) 10/07/2011 at 3:52 pm #

    Ahhhh… look at that cupcake! And swings to accompany it? Amazing.

  2. Sabina 10/08/2011 at 1:08 pm #

    Awesome guide. All those shops are making me want to go to Chicago. None of the cupcake shops in NYC have swings.

  3. My charming sister 10/08/2011 at 10:48 pm #

    So cool, these images are beautiful and I love her hair!

  4. Lauren Helen 10/10/2011 at 4:09 pm #

    I love her – I’ve emailed her about how beautiful I think her hair is too. She’s gorgeous!


  5. Susan (ModCloth) 10/11/2011 at 11:13 am #

    Such a cute tour! Makes me really want to go back to Chicago. Last time I was there, I really loved the food at Longman & Eagle ( – the chicken & waffles was amazing! I also really loved the Renegade Handmade store in Wicker Park (

  6. nora 10/17/2011 at 9:25 am #

    Swedish Bakery in Andersonville is really nice. They have really good cupcakes as well as marzipan frog cakes (which sounds weird, but trust me they are awesome!). Also there is lots of shopping to do in Andersonville as well.

  7. Mandy 04/06/2012 at 3:24 pm #

    I love Knee Deep! When I went there they had a whole $1 rack of clothing. I bought so many clothes that day.

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