Guide to Spending 48 Hours in Chicago

If I am being completely honest Chicago has never been at the top of my travel list. There was no allure for me simply because of the negative things I heard about the city like how dirty it was, the safety, etc. Boy was I wrong…

londonhouse chicago rooftop the sweetest escapeEvery negative perception I had about Chicago immediately dissipated after my first night. The people are friendly, the food is amazing, and the city  is very clean! I highly recommend going for 3-4 days instead of cramming everything into one weekend, but that was my only option because a girl’s gotta work!

Luckily I have a wonderful friend that has been living in Chicago for the past two years and he was our tour guide for the whole weekend (thanks Baker!) Seriously so thankful we had him otherwise we would have spent most of our time getting lost instead of actually seeing the sights. He knew so many cool facts about the city and the best way to get around town. If you have friends in the cities you are visiting don’t be afraid to catch up with them and see if they can show you around! I went to Chicago with Jen, one of my best friends from work. She also loves traveling and we were so excited to do this trip together.

Use this as your ultimate “Chicago in a Weekend” guide for information on where to stay and what to do. I will dedicate a separate post just to eating in Chicago and all of the restaurants we went to.

chicagorooftopbarBest season to visit: Summer

Recommended number of days: 3-4

Airports: Chicago O’Hare or Midway

Transportation: Uber or you can use the train through the city

Favorite area: Riverwalk


londonhouse chicago the sweetest escapeWhere We Stayed

We were lucky enough to snag a room at the new LondonHouse Chicago for the weekend. The LondonHouse is a brand new luxury hotel (only two months old) located on Wacker Drive right across from Trump Tower. The customer service was great and our room was beautiful. The biggest draw to staying here is access to the rooftop bar with great views of the city. Since the hotel is still so new there is a six-week wait to even get a reservation for drinks on the rooftop. We snuck up early one morning just to check it out and take some pictures, next time we definitely plan on enjoying the view over dinner and drinks. If you are a Hilton Honors member you can use your points here like I did.



londonhouse front entrance

Views from the rooftop bar at the LondonHouse! If you plan on going this summer definitely call and make a reservation in advance since they are booking up quickly.

londonhouse chicago rooftop the sweetest escape



 1. Cloud Gate “The Bean” – Millennium Park

Probably the most iconic landmark in Chicago, The Bean is a stainless steel sculpture in the middle of Millennium Park. You’ve probably seen this a million times on your friend’s Instagram, but it’s worth seeing in real life. We specifically wanted pictures with no tourists in the way so our first morning in Chicago we woke up at 5 a.m. to better our chances of beating the crowds. Luckily there were only a few other photographers lingering around and with a tad bit of patience we were able to get a couple of shots with nobody in the background!


cloud gate the bean chicago the sweetest escape

the bean cloud gate chicago the sweetest thing

2. Lincoln Park Zoo

The Lincoln Park Zoo is the only free zoo in Chicago, you can’t miss walking through for an hour or so and checking out the gorillas, giraffes, and lions! I haven’t been to Chicago in the winter, but apparently there are indoor enclosures so you can see the animals 365 days a year. There are several blocks of beautiful houses in the area and you can walk through the park to reach the lake. I really loved this area of the city and hope to spend more time walking around the park during my next trip.

lincoln park zoo chicago the sweetest escapeLincoln Park zoo chicago the sweetest escape

wrigley field bleachers chicago3. Wrigley Field/Wrigleyville

Unfortunately we weren’t able to make a game because the Cubs were away, but regardless of the schedule you have to see Wrigley Field while you’re in Chicago. Baseball fan or not it’s an iconic American landmark so you’ll want to get a picture or two. There are many old-school game day bars in Wrigleyville and newer places that are great for Sunday Funday. My friend that was showing us around also graduated from the University of Alabama so we obviously had to visit the Houndstooth Saloon in Wrigleyville to get our Bama fix.

Next time I visit I want to make sure I can go for a Cubs game, I can only imagine how fun it would be based off everything he told us!

wrigley field main entrance the sweetest escapehoundstoothsaloon
4. The Signature Lounge

The Signature Lounge at 96th gives you sweeping views of the city. We went at night and we saw a whole firework show off Navy Pier! Most people opt to do the Sky Deck in Willis Tower. Basic admission is $22 and that will get you to the top of the tower where you can step in the glass “ledge” and take pictures.

Our friend recommended going to The Signature Lounge instead, slightly less touristy plus you get to sit and have a drink while you enjoy the view! If you choose to do just one or both make sure you bring your camera.
chicago skyline at night the sweetest escape

5. Architectural Boat Tour 

chicagobridgeThis was one of my favorite things we did while in Chicago. It’s always nice to squeeze in a little education about the place you are visiting. Chicago is a great mix of old and new architecture so it was cool to learn about the history of each building. We went with Wendella Tours, but there are several other options to choose from. Tickets were $35 and the tour lasts for 75 minutes. Our guide was a native Chicagoan and knew a lot of interesting facts about the city. Since it gets pretty hot in the summer I would suggest either going first thing in the morning like we did or at the end of the day because there is no shade on the boat!





chicagotour2chicagoboattour3chicago riverboat tour the sweetest escape

6. Taste of Chicago

The main reason we choose this weekend in particular to visit Chicago! We heard Taste of Chicago is one of the best festivals in the city to go to and since we are both foodies we couldn’t pass up the chance to check it out. All of the well-known restaurants that would be on your Chicago bucket list were there! It’s a 5-day festival held right in the middle of Millennium Park with food trucks, concerts, beer gardens, and other activities. You pay per ticket and each “taste” costs between 4-5 tickets or you can buy a full serving of a particular dish for more.

Whatever weekend you are visiting Chicago you should check out the calendar and see what events are happening around the city, chances are there is something going on. I hear there are many festivals, farmer’s markets, and concerts (Lollapalooza!) during summer.

tasteofchicagotaste of chicago 2016 the sweetest escape7ffb8c2d-0a30-46c2-891e-2b4108dfdb8d


Basically I love summertime Chi and I can’t wait to go back! I’m not quite sure I would survive a winter there, but I could always stay inside and eat deep dish pizza for breakfast, lunch, and dinner.

On that note stay tuned for my Chicago Food post later this week!

Travel Well,


One thought on “Guide to Spending 48 Hours in Chicago

  1. Pingback: Chicago Food Guide – California Roots & Cowboy Boots

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