Chicago Travel Ideas

This weekend I got to do a little girls getaway with my family to Chicago, which was really FUN! I grew up going to Chicago almost every month from Wisconsin (I live about an hour north of Milwaukee, and two hours north of Chicago) to visit my grandparents, aunts, uncles, and cousins. We really don't have many relatives that live in the Wisconsin area, so I always felt like Chicago was my second home where I could go to be with family. We never really did a whole lot of "tourist-y" kinds of things when we were in the city though because it was just like HOME, where you usually don't appreciate all the activities that your area has to offer. BUT, for this trip, we decided to act like tourists and see the sights. It was an absolute BLAST, and made me fall in love with Chicago all over again, but from the lens of a visitor! If you haven't been to this city, you are missing out! It has so many amazing things to experience. Below is a little travel guide of things that we got to do this weekend.

1.Lodging: The Chicago Athletic Association

My uncle gets some really great deals at some of the hotels downtown through his company, so we decided to stay at The Chicago Athletic Association Hotel. The rooms were nice, BUT the coolest part of this hotel is the beautiful gothic architecture. I just got a new camera, so I was having fun practicing taking pictures of the interior of the building- there were so many neat features to take in! It was built in the 1890s, and they have renovated and preserved so much of the original character that makes it such a gorgeous site to see. PLUS, the big bonus here is that the hotel is right on Michigan Avenue, which is a huge shopping mecca for all of you out there who LOVE to shop like me! All of the best shops are within walking distance, so you can't ask for much more.

2.Shopping on Magnificent Mile and More

If you scope out locations to travel based on shopping alone, you definitely will NOT be disappointed with Chicago. Shopping has ALWAYS been one of the main activities that we would partake in when visiting family in Chicago growing up-so this activity is not new to me, HAH! There are so many cool streets and neighborhoods that you can shop in, AND shopping in this city could take you the entire weekend and then some! My favorite place to shop in downtown Chicago has always been on Michigan Avenue- which they have coined the Magnificent Mile. You have your high end designer stores, like Louis Vuitton and Burberry, BUT you also have your Express store or Forever 21 options too. There is such a wide range of options, that sometimes it can feel overwhelming...BUT, definitely overwhelming in a good way! Of course I have to veer off of Michigan Avenue a bit to hit up one of my favorite stores- NORDSTROM (which is close by on East Grand Avenue). If you want some more extensive ideas on where to shop other than Michigan Avenue, check out this article as well . It has some REALLY great information on where to go, ladies!

3.Chicago Architecture Foundation River Cruise

Out of all of the hundreds of times that I have gone to Chicago, I have never done a single tour! I know that sounds crazy, but when you are staying with local Chicagoans, you tend to not do these kinds of things like I said before. BUT even my aunt, who is a local, really enjoyed and learned a lot about Chicago from this tour this weekend. It's a 75 minute river cruise that only costs $47 for daytime rides and $52 during twilight hours. You get to cruise up and down the Chicago River and have AWESOME views of the most famous historical and new buildings in the city. I got some seriously great practice taking pictures with my camera and learned so much about the history of Chicago at the same time! This is definitely a great option for out-of-towners, my friends!

Views of the amazing Chicago skyline from the river cruise.

4.Dinner at Joe's

If you are a seafood lover, you MUST try Joe's! We had dinner there on Saturday night after all of our shopping and excursions, and the food was absolutely delicious. I had the crab bisque soup and crab cakes as my entree, and I savored every bite. So YUMMY! All of us gals ordered seafood, and we all really enjoyed our meals. You do have to dress up a bit, which is never a problem for me because you don't have to ask me twice to get GLAMMED up. BUT, I thought I'd give you a heads up if you do choose to go there. Another word of advice for ANY and ALL restaurants downtown Chicago- MAKE RESERVATIONS far in advance, because seriously the popular places book up VERY quickly! Here are some other really delish and popular dining options to choose from downtown...

  1. BLVD
  2. Bavettes
  3. Bellemore
  4. Oriole
  5. Smyth and The Loyalist
  6. GT Fish and Oyster
  7. Boka
  8. Le Colonial
  9. S.K.Y.
  10. Sepia

5.Brunching at Cindy's

Sunday morning we woke up and, of course, needed to do the brunch thing! The top floor of the Chicago Athletic Association is actually a club at night (HOLY COW was there a line to get into that club), BUT it also doubles as a restaurant during the day called Cindy's. All of us thought the food was just decent, however, MAN was the view up there amazing!!! That view was seriously worth it! You can eat inside or out, and it overlooks Millennium Park and Lake Michigan, with an awesome skyline view to boot! I could have stayed up there and chilled with a mimosa all day.

View from Cindy's rooftop- Can you see The Bean?? So fun!

6.Millennium Park

Millennium Park is such a fun little tourist spot to check out. On Saturday night, they had a free concert in the park and a little festival going on, and it had just a fun vibe about it. Check out the calendar of events at Millennium Park in the link above. Of course, you have to take the typical, yet fun, picture of yourself next to the Cloud Gate sculpture, lovingly known as The Bean, because YES it seriously looks just like a bean. BUT, aside from that, this park is just a fun place to people watch and stroll around and relax!

The Bean
View heading out of Millennium Park, so classic CHICAGO with the "L" Train and all.


Have you guys ever been to Eataly? They have five different locations across the U.S., and this was my first visit. I had heard so many great things about Eataly, so I was excited to explore ALL things Italian in this two floor spectacle! They have little restaurants inside to eat at; they have little stations to try food at; they have groceries and everything and anything else you can imagine! My sister and I tried the pizza focaccia breads, and they were to die for! YUM! We also went around sampling all the delicious cheeses and meats until our bellies were full. I would definitely make my way back there again!

CHEERS from Eataly!

8.Lincoln Park Conservatory and Gardens

So we didn't actually go to the conservatory this weekend, but if you read my post from a few weeks ago, you probably noticed that I was in Chicago for a wedding then as well. We stopped at the Lincoln Park Conservatory to take pictures for Ashley and Devin's wedding, and WOW, it was an absolutely beautiful place for photos! If you are a garden and flower lover, you should definitely add this to your to-do list when you make it to Chicago! There are rooms and rooms of just gorgeous plants, foliage, and flowers. You won't be disappointed!

9.Lincoln Park Zoo

Another spot that Aaron and I stopped a few weeks back during the wedding weekend trip, was the Lincoln Park Zoo. OK, who doesn't love going to the zoo?? I always love checking out the animals at the zoo, BUT this place also has some amazing architecture and flower gardens as well to see. Plus the juxtaposition of these wild animals with the city skyline in the background is just such a neat thing, in my opinion! Definitely worth the little jaunt over to that area of Chicago.

So there you have it, my friends...just a few travel ideas for you if you ever make it to the Midwest and Chicago area. I just LOVE this city so much because it reminds me of family and growing up- BUT, I also love it because it has so many NEAT features and activities to do! You will definitely not be bored if you decide to visit. PLUS, it's easy to get around with their train system, and of course other forms of public transportation are available (HELLO UBER, so easy) as well...OR, just walk! OH, and if you guys decide to take a trip to the Midwest, don't forget to stop in Milwaukee as well! Maybe I'm a biased Wisconsinite, BUT Milwaukee is one of my other favorite little cities. BUT, that is for a future blog post. Also, for the NEAR future, as in Thursday, I will be linking and posting about the FUN rainbow colored trend you are seeing in clothing lately, like my off the shoulder top in the pics. BUT for now, have a great Tuesday, all.


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