We had such a great time in Chicago, hoping the weather would be great for us. It did not disappoint, weather turned out to be in the high 70’s for a couple of days and then dropped in the 60’s. According to the locals we were told the weather had not been that warm since September.  We were able to rent bicycles for a couple of days and ride along Lake Michigan, they have a great walking biking path- I have included the link below if you are interested in renting bicycles.

On our vacations we do our best to find things off the beaten path, and taking a train to the airport and getting around the city is always interesting.  We love to use the app YELP to find great little restaurants and bars around the city- tons of reviews on this website, check out the speak easy bars around Chicago as well.  I also highly recommend doing an architecture tour on the river, although its kinda expensive you can find some great deals on groupon for 50% off.  The architecture tour is listed below and included a link for you to check out.

Our favorite things to do in


Outdoor Walking and Biking

Lake Michigan is located right next to the heart of Chicago so there are great paths that are desigated either for bikers or walkers.  On a sunny day in Chicago you can find tons of people out on this Lake Front Path.  This path is 22 miles long and is primarly flat, so its an easy ride.  Below is a link to the Path.  I have also included a bike rental link below, this bicycle shop is very close to the path as well as to the Navy Pier


Restaurants and Bars

Well not sure where to start but there are a ton of restaurants and bars in downtown Chicago.  We love to visit local dive bars as well as “secret bars”.  I do have to say that I could not leave Chicago without having deep dish pizza- hmmmm well I could pass on that, it was not as good as it sounds.  Check out the link below to find more fun secret bars to check out. 



Jazz Music

So Chicago is known for its Jazz music, and it does not disappoint.  There are a ton of nightlife jazz restaurants and lounges in Chicago.  One of the lounges we went to was “Pops for Champagne”, there menu was rather expensive but I guess you can expect that in Chicago.  Pops also has a lounge downstairs if the music gets too loud called “Watershed”, the night we went there it was completely dead but then again we were there on Easter Sunday, we told the bartendar to make us something fruity and he did not disappoint.  Check out the link below.

Chicago River Cruise and Walk

Also do not miss out on doing an Architecture River Cruise, this is a 90 minute tour and there is so much information on the tour you will not be disappointed. This was one of our highlights of our trip to Chicago, viewing the building from the River was really breathtaking. This tour costs $49 it includes drinks and cookies, but check on groupon we booked our for $29.

So at one point, back in the 1800’s the River was a stinky slimy River that you wouldn’t dare want to get near.  The city has transformed this stinky river into something quite spectacular, with its high rise buildings and great restaurants and bars along the river its definitely a must do when you are in Chicago.  Take a stroll in the evening to catch a glimpse of the buildings lit up with the reflection on the river, you can get some great pictures for sure.


There is one street that is very famous in Chicago, it is called the Magnificent Mile Street. This is a 13 block stretch of restaurants and high end shops with more than 460 stores, 275 restaurants and 60 hotels.  There is most certainly something there for everyone.  If you are just a window shopper there is a ton to see along this street and with the beautiful architectural buildings all around you can’t help but to enjoy yourself.


Oh my goodness, just have no idea where to start with this!  From going to a Chicago Cubs game to enjoying a broadway show or taking in a magic show- ok so this is where I’m going with this. 

We booked an evening with a magic show, there were 5 different magicians that would do card and coin tricks right at your table while listening to a live band play jazz. Not only do you get 1 magician coming to your table but each one of the magicians will come over and amaze you.  This is one of the best magic shows we have been to, so fun to see everything up close.  Again we booked through groupon tickets range from $11-$24 depending on the day of the week you book.  This club is located about a 20-25 minute train ride from downtown Chicago.  I will list the link below.

Did You Know?

Gotham City

Chicago was the inspiration to the Batman movie, in fact they filmed some of the movie in Chicago.

Route 66

Fascinating fact is that Route 66 begins in Chicago and travels through Missouri, Oklahoma, Texas, New Mexico, ARIZONA, and California.

Navy Pier

The first ferris wheel was introduced in 1893 at the Chicago Worlds Fair.  The ferris wheel at the Navy Pier is actually modeled after the very first one in Chicago, kinda makes it special.

Travel Umbrella

Best Travel Umbrella, folds up to the size of a small umbrella, 2 people can easily stand under this umbrella without any problems. This is very affordable through amazon, pricing under $15 for this product.


Sunscreen is essential year round. Weather you’re baking at a Chicago Cubs game or strolling through the Magnificient Mile Street, sunscreen is a must have. This Oil-free EltaMD UV Clear facial sunscreen is recommended by dermatologists because it helps calm and protect sensitive skin types prone to acne, rosacea and discoloration. This mineral-based face sunscreen is lightweight and silky.



The Chicago sunshine means that sunglasses are an absolute must. These lightweight, stylish glasses are essential for any trip.


Beach Bag

Everyone needs a great beach bag, take this to the beach along the Michigan River or to the great Parks in Chicago with the bag being made out of mesh its very easy to get the sand and grass out of the bag.



Cloud Gate, commonly known as “The Bean”

Yes this is a tourist attraction, but its well worth the time to check it out.  This is located in Millenium Park, which is a great place to go for families, they even have minature golf there.  This sculpture is made up of 168 steel plates.  Hey, its FREE so why not check it out!  

Beautiful Weather

Head over to the Lincoln Park Zoo to check out the animals, this is another FREE place to go for families and then head into the Lincoln Park Conservatory to check out all the lush flowers, ferns and exotic plants, great picture opportunities there.

Billy Goat Tavern

This tavern is very unique to Chicago, this is where you go to watch the Chicago Cubs play if you are not at the actual game.  This is also the site of a famous skit that was done on Saturday Night Live…. Cheezborger, Cheezborger, Cheezborger.  The tavern is under the bridge and is a must see when visiting Chicago.


Our hotel in Chicago

We chose to stay at The AC Hotel near downtown Chicago, this is a newly acquired hotel chain by Marriott.  This was a great location, a couple of blocks off from the Magnificent Mile street and within a 15 minute walk to the river.   Very clean hotel, beds were comfortable and the gym was a decent size.   The do have a breakfast buffet, but no eggs cooked to order cost is $15 per person.  What we like about this hotel is that you are in the center of downtown Chicago within a couple of blocks, in fact when we took the train back to the airport we walked about 3 blocks and ended up taking the L Train to Ohare Airport, cost was $2.50 per person, much cheaper than taking an Uber and then you get the experience of riding on the train.

There train system is really easy to get around the city, I would highly suggest using the train.  I have included the link to the website so you can check out the maps and easiest way to get around.  Also ask the front desk at your hotel as well they will be able to give you the best directions to navigate through Chicago.




Get updates, travel tips, and more straight to your inbox!