Out and about in Chicago


Earlier this summer, we asked two Vera Bradley gals to turn their business trip to the Windy City into a (fashionable) travel log. Given the recent arrival of several outstanding new styles, they were happy to oblige and the result was a firsthand account of how a weekday conference a few cities away can be a commuter’s dream with the right luggage pieces and accessories. Libby, Social Media Coordinator, shares the days’ events.

In June, Web Marketing Coordinator Samantha and I packed our bags and headed north (from Fort Wayne, IN) to catch the train into Chicago. On the agenda: Attend the Internet Retailer conference, the world’s largest e-commerce conference, and of course, take in a few of the sights.

The perfect trip requires the perfect luggage, and trust me, we had that part covered! I packed the bulk of my belongings in a Weekender and 22” Rolling Carry On in Paisley Meets Plaid. On my arm, I kept my laptop in the Laptop Travel Tote (also in Paisley Meets Plaid) and an On the Go in Black (available August 30). The bags were perfect! I had plenty of space for my conference outfits and even managed to throw some workout clothes in there.


While the 22” Rolling Carry On has a special spot in the front for a laptop, I had the Laptop Travel Tote, so I used the padded sleeve for stashing extra Totes instead. Hey, a girl’s gotta have options, right?

As for the Weekender, I am officially a major fan of the trolley sleeve feature.  It slides right over the Rolling Carry On handle, and I could easily manage my luggage. As a serial over-packer, I really appreciate being mobile with multiple bags.

loving the Trolley Sleeve

Samantha opted for pieces in Indigo Pop and Black, with a burst of color provided by her Va Va Bloom Hipster. Her Carry-On Rolling Satchel in Indigo Pop was lightweight but multi-functioning: “I was able to carry it over my shoulder as a satchel or turn it into rolling luggage with the hidden T-bar trolley,” she said. Her favorite piece was the 22” Spinner in Black (available August 30), because it made getting from train to taxi a breeze! She also joined Team Trolley Sleeve after discovering the joy of simply topping her Roll Along Work Bag (also available August 30) on the 22” Spinner.

Sam packing for Chicago

Samantha raved about her Hipster: “I never travel without a Hipster! It’s just big enough to hold my phone, a wallet and a bottle of water so that I can stay hands free while I sightsee.”

We were officially packed and ready to hit the road! Or should I say, tracks?


Admittedly nervous about navigating the Chicago highways, we decided to travel by train. The trip from Fort Wayne to Union Station was about 4 hours; time easily passed chatting about our college study abroad adventures (me: Spain, her: Italy) and researching delicious Chicago eateries.

Sam, Vera Bradley Web Coordinator

Since the conference didn’t start until the next day, we hit the ground running. First up, a leisurely brunch at Yolk. The weather was perfect; not too chilly, not too hot, with a clear blue sky. We strolled along Lake Michigan, taking in Chicago landmarks like the Shedd Aquarium, Clarence Buckingham Memorial Fountain and Navy Pier.

Yolk, in Chicago
Sam, Vera Bradley Web Coordinator

It’s no secret that we at Vera Bradley love our sweet treats, so we definitely made time for a trip to Sprinkles Cupcakes. I was infatuated with the red velvet. And finally, no trip to Chicago is complete without pictures in “The Bean” in Millennium Park.


the bean, Chicago

We had a blast in the city (and learned a thing or two at the conference, too). Before we knew it, we were standing next to those familiar prints back at Union Station. Until next time, Chicago!

Union Station

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15 Responses to Out and about in Chicago

  1. emme27 says:

    Good luck girls with your studies abroad. Obviously you will be going in style with Vera.

  2. Mary Verdun says:

    Great story but they brought too many clothes

  3. allison says:

    so cool and I want those first bags if only they were not so much

  4. dotmoody says:

    Lovin the Paisley Meets Plad luggage!! Such lucky woman to be a part of the Vera Bradley family 🙂

  5. Jeanette says:

    I thought the weekender didn’t have a trolley sleeve so how can she be a trolley sleeve fan? Did I miss something? I wish the weekender did have the trolley sleeve since its bigger than the metropolitan.

    • Janice says:

      It’s the travel overnighter with the trolley sleeve – I thought the same thing and about turned my weekender inside out until I realized it was a different bag that has the sleeve!

  6. Pat says:

    Does the weekender have a slip that slides over your rolling cart?

  7. Mary says:

    I’m headed to Chicago for a long weekend in Sept. Traveling with Vera rolling luggage would be such a stylish way to arrive in the city.

  8. Laurie says:

    Love the Weekender and Hipster for travel also. Hard to belive you needed all of that luggage for just a few days though. I travelled through Japan for a month with just the weekender and hipster (and had enough room to bring gifts back for family and friends).

  9. Helen Semethy says:

    I have used the grand weekender in night and day for several years going
    to Europe and it is perfect. I also use the Miller bag and put my purse inside
    therefore I can carry on more which was great when due to problems with
    a plane it took us three days instead of one to get to Europe last December.
    Everywhere we went people stopped us and wanted to know where we got
    our luggage – grand weekended, Miller bag and the duffel bag. I wish I could
    have found somewhere a rolling bag om night and day. I wish someone could
    make me one.

  10. Jacqui says:

    The luggage is my next purchase! Chicago is amazing! Everything is better with Vera!

  11. Karen Remillard says:

    My Vera duffel has logged so many trips to Europe and around the U.S. that it should have a passport. It just celebrated it’s ninth birthday with a new toiletries bag and a train trip from MA to PA. (The toiletries’ bag in the matching pattern had long since lost it’s plastic lining so I cut out the lining and repurposed it to hold my hairbrush, clips, etc.) I love taking the duffel as a carry on because of it’s relatively unstructured style that allows to fit within the carry on guidelines box at the airport. And if I really stuff it full for the return trip, then I put a strap around it and check for the return. Then I just use of the reusable nylon shopping totes that I always carry with me for a carry on! I NEVER travel without Vera

  12. sierra k. says:

    looks like a great trip in the city! I’d travel VB style with you ladies any day : )

    p.s. sprinkles cupcakes are my favorite here in NYC!

  13. Janice says:

    I have the Weekender bag and was wondering how could I have missed that trolley sleeve – it must be really well concealed. But the weekender doesn’t have that feature – its the travel overnighter that does. Ay chance the Weekender will be modified to add the trolley sleeve?

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