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A Couple’s Weekend Travel Guide To Chicago + Giveaway with Betsy Boo’s Boutique

A Couple's Weekend Travel Guide To Chicago

This week has been a busy week. My hubby and I celebrated our two-year anniversary! We had an amazing night, having wine and dinner with a beautiful sunset view on the water, and then topped it off with our very own s’mores bar. It was absolutely perfect. If you didn’t get to check it out on Snapchat, I posted this picture of my outfit and the view on my Instagram. Two weeks ago we went to Chicago for a little weekend getaway to mark our second year of marriage and our first trip out of the state without the baby. It was hard for us to leave the little guy, but we knew he was in good hands with our family. Those three days in Chicago were amazing. It was one of the most beautiful cities I have ever been  to, great weather, delicious food, and we stayed in one of the best hotels in Chicago. There are so many things to do and see especially in three days in Chicago, so I teamed up with the Betsy Boo’s Boutique to give you the best tips on what to wear, where to go, places to eat, and where to stay from a couple’s perspective.

A Couple's Weekend Travel Guide To ChicagoA Couple's Weekend Travel Guide To ChicagoA Couple's Weekend Travel Guide To Chicago   A Couple's Weekend Travel Guide To Chicago

What to Wear:

When visiting in Chicago in the summer, remember these two things:

You will be walking every where, but everything is walking distance if you stay in the right place.

The weather is beautiful, but can get very hot.

Betsy Boo’s Boutique is an online boutique offering trendy and stylish ready to wear clothing for women. For the first day there, I wore this adorable floral off the shoulder top from Betsy Boo’s Boutique and comfy shorts and sandals to match. This top is a nice light weight breathable material that allows you to stay cool when walking around all day.  My hubby wore a white short sleeve button down, canvas shoes, and hybrid shorts.

A Couple's Weekend Travel Guide To ChicagoA Couple's Weekend Travel Guide To ChicagoA Couple's Weekend Travel Guide To ChicagoA Couple's Weekend Travel Guide To Chicago

For the second day I wore this adorable paisley print dress, also from Betsy Boo Boutique, that can be worn on the shoulder during the day with sandals, and dressed up off the shoulder with heels, earrings, an envelope clutch for a nice dinner out. My hubby wore jeans, a short sleeve button up, and Tom’s oxford shoes.

On the last day before we left, we explored Maggie Daley Park and the pier and wore this comfy Wife, Mom, Boss tee with white tennis shoes, and my go to denim cut offs for summer. It’s the perfect throw and go shirt for hiking in the park. It’s currently my go to shirt when it comes to casual comfort. Plus it explains who I am in three words. 😉 Check out Betsy Boo Boutique for all their cute tops and dresses for the perfect travel getaway look. A Couple's Weekend Travel Guide To ChicagoA Couple's Weekend Travel Guide To Chicago

Where to go:

There’s so many places to go in Chicago. The parks alone could have been two days to fully explore it. My hubby and I did as much as we could for the time that we had, even though we know there is much more that we want to do next time we visit. Here is my top eight things to do when you visit:

1.Ohio Street Beach

2. Take a Taxi Ride on the River

3. Walk down the River Walk

4. Shop on the Magnificent Mile

5. Go to Millennium Park and take a picture at Cloud Gate

6. Have drinks and check out the view at the John Hancock Center

7. Ride the ferris wheel at Navy Pier

8. Party on a rooftop bar

A Couple's Weekend Travel Guide To Chicago

The view from Navy Pier. It is more for the kids, I think, but it was great to walk around and see all the boats going in and out to the lake.

Below is Ohio Street Beach. It was beautiful, and if I lived in Chicago I would be here every weekend. There were tons of boats on the lake enjoying the beautiful weather.
A Couple's Weekend Travel Guide To Chicago

A Couple's Weekend Travel Guide To Chicago  

A Couple's Weekend Travel Guide To Chicago

Millennium Park and Cloud Gate. This park is huge, and there is so much to do. It is definitely crowded during the afternoons, so I recommend going earlier during the day. I could have spent a whole day here exploring, but we didn’t have that much time, so a good photo-op at the bean was what we settled on.

Below is the view from the John Hancock tower, one of the tallest towers in Chicago. Here’s what you need to know about this tower and the Sears Tower, the will charge you $20 a person to sit on their sky box, which is an extended view of the skyline. However from a couples point of view, save the $20 and do what we did. Go to the John Hancock tower and go to the bar on the 96th floor. The views are just as amazing and you can relax with your love and have a drink. Also there isn’t a long wait to go to the bar, unlike the 360 observatory deck or Willis Tower. If I was to do it any different I would have gone down to the 95th floor where the restaurant was. It is less crowded than the bar and you can get better views because the restaurant wraps around half the building.

A Couple's Weekend Travel Guide To Chicago

The River Walk is beautiful and nice place to stroll around during sunset. There are tons of places to eat and drink along the River Walk. It has the prettiest photo ops. I really wish we had time to take the River Taxi. It is cheaper and less crowded than boat tours, and plus you get to see Chicago from a local’s perspective. It would have been great to see the extent of the city through the river, than just by foot. If you like adventures, you can also do a kayak tour down the river. The picture below was taken at the London House Rooftop Bar on the River Walk. My hubby and I went there with friends for a fun adult night out. However since it is a fairly new bar, go early because the lines are long.A Couple's Weekend Travel Guide To Chicago

What to Eat:

There are so many great places to eat in Chicago, and there are two things Chicago is known for, their deep dish pizza, and their hot dogs. There’s nothing like experiencing those two things in Chicago. Below are a few places we went and really enjoyed when we were there.

A Couple's Weekend Travel Guide To Chicago

A Couple's Weekend Travel Guide To Chicago

When  we arrived in Chicago the first place we went to eat was Eggy’s Diner. We wanted to go to the famous Wild Berry Cafe but the wait was over an hour long. I’m glad we decided to go to Eggy’s Diner instead because the food was absolutely amazing. There was not a thing on that menu that we did not clear our plates. It was so good we went twice! Wild Berry was not everything I thought it would be when I went, I think it was because it was too touristy. Eggy’s was a great alternative. You could tell it was more where the locals ate, and it was right across a cute little dog park.

Another place to go to is Molly’s Cupcakes. On our way back from walking from Navy Pier we stopped by there because I am a big fan of cupcakes and the show Cupcake Wars. It was hard to choose only two cupcakes to take home with us. But they were worth it, and made a great snack after coming home from the bars.

A Couple's Weekend Travel Guide To ChicagoA Couple's Weekend Travel Guide To Chicago

Now on to the pizza and the hot dogs! Let’s just say my hubby and I are foodies and we definitely stuffed our face silly while we were in Chicago. For Pizza you have to go their world-famous Giordano’s and try their delicious deep dish pizza. I was in Cheese heaven! My hubby and I could only eat half the pizza while we were there, but I’m glad we had left overs because it made a perfect late night snack. P.S. Be warned it is a 45 minute wait for your pizza as they do make it fresh! For the hot dog we went to the River Walk and ate at the restaurant Chicago Burger Company. My husband had the burger and I had the Chicago Dog. Let just say our meals didn’t last ten minutes in front of us. It was so good, and we had a great view of the river.

A Couple's Weekend Travel Guide To Chicago

Where to Stay:

For our stay we had the privileged to have a complimentary stay at the Fairmont Chicago. When we first entered we were treated by friendly door staff and concierge. They brought our bags to our room where we were upgraded to a signature sweet where we had a beautiful view of  Grant/Millennium Parks. We loved being able to look out our window and see the Taste of Chicago, and to map out our next adventure on what we would see next. The hotel was in the most central location to all the places to be in Chicago. I didn’t realize till we got there how close we were to everything. We literally walked everywhere because we were less than a mile from everything we wanted to do. The only time we rented a taxi were the nights I decided to dress up and wear heels. Even then the taxi rides were less than $10 to get anywhere.

A Couple's Weekend Travel Guide To Chicago

A Couple's Weekend Travel Guide To Chicago

The rooms were immaculate and so spacious. We slept like kings and queens on this bed. It was hard for us to want to get up some days. Lets just say there were plenty of naps taken here. We were surprised by complimentary wine and chocolate strawberries to celebrate our anniversary. But I think the best part was, they made it feel extra special by having a framed family picture of us next to our bed. It was such a thoughtful gift and sweet though from the hotel, and as a momma I really appreciated it. It was the gift I cherished the most on that trip, and now sits in our living room today. Thank you Fairmont for the complimentary stay, we really enjoyed it!

A Couple's Weekend Travel Guide To ChicagoA Couple's Weekend Travel Guide To Chicago

Overall Chicago was a beautiful city, and the perfect getaway for couples. I highly recommend it for anyone going to visit. My hubby and I have said multiple times we plan to go back with a boat and just sail around Lake Michigan and up and down the River Walk in Chicago. If you have any questions about our stay please feel free to ask away in the comment below. Don’t forget to check out our fun mini video of our trip below! For all my wonderful readers, make sure to stay tuned on my Instagram, as I’ve paired up with Betsy Boo’s Boutique to give one lucky reader a chance to win a gift card to shop at Betsy Boo’s Boutique. Giveaway will end Sunday the 24th. Make sure to check to follow them on Instagram to enter to win. Good luck!

<3 Dawn

Thank you Betsy Boo’s Boutique  for sponsoring this post.  As always all thoughts and opinions are mine alone. Thank you for supporting those who support this blog.

A Couple's Weekend Travel Guide To Chicago

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