Chicago Travel Guide: A girls' weekend in the Windy City

Just a few weeks ago, 8 girls and I flew from several locations on the east coast to Chicago for a girls long weekend to celebrate one of Allie’s last weekends as a non married woman. As most of us had not been to the windy city, I made sure we fit in lots of tourist activities along with girly group time.

While this is not a super crafty or creative post, I hope its contents might help others plan a girls or bachelorette windy in Chicago.

Tourist Fun:

Ride the Ferris Wheel! The first day we got there, it was nice and sunny and warm. I had bought tickets online prior to the ticket to tour their big tourist attraction, the Navy Pier Ferris Wheel. While I would recommend taking a ride, where you can see the view in the above photo, just buy the tickets when you get there and don’t buy them before hand. They charge you a $1 per ticket transaction fee online, and it turned out we had to wait online anyway to get the tickets, which defeated the convenience I thought we’d have.

Visit the Zoo! We stayed in the River North area of the city so with a $15 cab ride (for all of us!) we made our way to the Lincoln Park Zoo. It’s a nice zoo, not much difference from most I’ve been to (and I’ve been to lots!) but it was great that it was free!

Take a tour! I would highly recommend the Chicago Trolley and Double Decker Signature Tour. With 14 stops, this bus system became a cheap and easy way to spend a jam packed day touring around. You could hop on and hop off at any of the stops to spend as much time as you wanted at each stop.

We used this tour to get us around to lots of the highlights: the Bean in millennium Park, Willis Tower, The Chicago Theater, the Buckingham Fountain, just to name a few. The ticket to the tour also included a coupon book, which got us free samples of the Garrett’s popcorn Chicago mix (a pretty decent sized sample!), a free cookie at The Corner Bakery and a bunch of other discounts. We also used a coupon in the book for a later night (seen below).

We went the extra step and purchased the add on option of the Sky Deck tour on the Willis Tower (previously known as the Sears tower). On top of the 103 floors were some beautiful views of the city.

There were also glass boxes where you stand out over the city below, which was a pretty fun experience for all except one who was afraid of heights.

Right outside the Tower were these yarn bombed balls and tree branches that we thought were so fun!

Restaurants:

Harry Caray’s – We had lunch at their Navy Pier location where most of our crew sipped their Wildberry Dacquris, snacked on the kettle chips and had the recommended Italian Beef sandwiches. Our crew seemed to enjoy all three!

Quartino – I had been recommended this restaurant stating it was great for group as it’s small plates that are shared amongst the table. That recommendation was dead on! We sampled and shared a bunch of Italian goodies, a delicious white wine sangria, sipped on flavorful limoncello and indulged in zeppoles for dessert! We made a reservation before hand and were seated quickly upon arrival. Our meal came out so fast that we were done before we knew it! It was super affordable to eat as a group and I’d highly recommend trying this place out for yourself!

Moe’s Cantina – This was another recommendation and since it was Cinco de Mayo weekend when we went, I thought Mexican had to be on the menu. We were surprised that we were somewhat laughed at when we ordered the Parrillada de Carnes (Rib-eye steak, short ribs, skirt steak, bone-in chicken, mixed vegetables, pineapple, Spanish rice, black beans, mini corn tortillas served on a mini table top grill), but she mentioned it wasn’t something typically enjoyed by a group of girls. Well these girls loved their meat and shared pretty much the entire mini grill it came on!

Cantina Laredo– Since we feasted on a platter of grilled meats, the girls didn’t feel like they got enjoy Mexican on this festive weekend. We enjoyed lunch here at Cantina Laredo ON Cinco de Mayo, where their Cinco Ritas (Giro Silver Tequila by Sauza, Hornitos, Herradura and Cazadores Silver Tequilas with Cointreau, lime juice and agave nectar) were only $5 instead of the usual $11.75. Get the guacamole! It’s freshly made on a cart that comes to you!

Giordanos – It wouldn’t be a true Chicago experience if we didn’t try out the famous Chicago style deep dished pizza, which we enjoyed for lunch at Giordanos along our tour.

Fun:

Howl at the Moon – Of course, I did mention it was a bachelorette weekend, so one night we all got dolled up with cocktail dresses and heels, had Allie sport a bachelorette sash and made our way to this super fun dueling piano bar. The cover charge was $10, but we had “2 free admission” tickets in our coupon book from the tour so we got in for free! They are known for this “Howlin’ Buckets” where you share your fruity drink through colorful swirly straws.

Hub 51 – After one of our Mexican dinner, we stopped over at the local bar from our hotel to enjoy a drink before bed. Little did we know that bringing a bachelorette along for the ride meant free Hub Bombs, a sweet shot! Share a pitcher of their sweet mixed drinks if you go with a group!