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Too Many Reasons for you to Visit Chicago (50 to be exact!)

And my exact itinerary!

*My Trip was sponsored by but none of the links in this post are affiliate links and the views and opinions expressed are my own.*

For some reason, when we think of travel and “goals” the locations are all abroad. We forget that the United States is huge and there are some many things here at home that we we should see! (1)

Chicago is one of those locations, it’s so close to home it can be done on a weekend for the extra busy (2), but there’s so much to do and see that if you have more time and availability, you can stay longer and you’ll never run out of things to do (3).

From Kansas City the flight is about an hour and fifteen to twenty minutes, short and sweet, so if you’re traveling with kids it’s a great option (4).

It’s about 2 hours from New York, 3 hours from Miami, 2 hours from Atlanta and 4 hours and 30 mins from Los Angeles, it’s pretty much close to everywhere (5).

In 2019, Chicago was voted #1 Best Large City in the United States by Conde Nast Traveler's Reader's Choice for the third year in a row (6). Simply put, people love the city!

Public transportation makes this big city feel more small town because it is so easy to get anywhere (7).

There are beaches! Chicago has more than 26 miles of shoreline in the city limits. May to September is the best time to check the 15 swimming beaches out (8).

Another fact, Chicago is home to the most breweries in the U.S. (9) so its the perfect place to sit and sip.

Besides drinks, Chicago is one of the best cities in the world to eat in. It has amazing restaurants ( over 7,300+) and 22 of which are Michelin starred, so if you're a foodie it is definitely a city not to be missed (10).

And now that you have all these reason's, here's my exact itinerary to help you plan. I will add the Instagram accounts for all the locations I visited so its easy for you to check the vibes! Follow them, and save their photos in a Chicago folder on insta so its easy for you to remember when you arrive in Chicago!


Arrived in Chicago at 11am,

Checked into hotel- London House Chicago (11):

Perfect Location, great views, beautifully decorated rooms, amazing restaurants on site, overall a great place to stay!

To check it out click here.

Or check out their photo's on Instagram:

Walked around Michigan Ave nearby- Shopping! (Chicago has amazing shopping and so many stores on michigan ave! so 12!)

6pm- Dinner, drinks and dessert at Offshore (13)

Offshore boasts the largest rooftop venue in the nation, and ya'll know how much I love views! Its beautiful inside, has an amazing bar and a world class kitchen. Cozy, delicious food, great drinks, vibes.


8am- Early morning visit to Skydeck Chicago (14)

Are you fearless? of course you are! Step out on the ledge at Skydeck into a glass box where you get the ultimate views. On a clear day, you can see 360 degree views and 4 states.

Pro tip: book breakfast on the ledge to get a glass box all to yourself in the morning and for an unforgettable dining experience.

10am- Chicago First Lady Cruise (15)

It seriously doesn't matter what time of year it is, this river cruise is a fun informational adventure. Its a great way to see the city and learn about the architecture, you get to see and learn details about all the cool buildings. There is an upper deck, and also an inside area with a bar and tables.

Noon- Lunch and tour of Starbucks Reserve (16)

If you're a coffee lover like me, you have to stop and experience this epic 35,000 sq foot, 5 story experience. There's everything from delicious food to an awesome bar.

2pm- Museum of Science and Industry (17)

If you're into science this place is for you. And right now (during the holidays) they have an amazing Christmas Around the World exhibit and other beautiful decorations that you wont want to miss. I only had a couple hours there but I definitely could have spent an entire day.

4pm more shopping and chill

5:30 pm Chicago Christmas Tree Lighting Ceremony ( City festivities are reason #18)

Again, there are always cool events going on in the city depending on the time of year. If you visit during the holidays the annual tree lighting ceremony should be on your list of things to do! We got to see a show, countdown to the lighting of the tree and see fireworks. The best part is its free.

7:30pm Dinner at The Gage (19)

About that amazing food I was telling you about above, the Gage is a great restaurant to experience it! One of Chicago's most booked restaurants, its a great place to eat on your visit. I really enjoyed the specialty cocktails.

9:30pm Santa Baby pop up bar (20)

Ready for the best Xmas themed bar ever? It is super extra, which is my favorite thing ever. There is 2 floors with great DJs, so many lights and decorations, and the themed drinks are perfect and over the top, just how I like them. You cant help but be in a good mood and get in the Christmas spirit when you stop here.


Sleep in from the night before!

10am- Chicago Food Planet brunch Crawl (21)

A brunch tour where you walk around Wrigleyville and learn about about Chicago while tasting local treats! so much fun, so informative, and so much good food! I loved the fact that at every stop we got a drink (mimosa, local beer, coffee, cocktail!) with the food we sampled and we got to try some dessert!

12:30- Christkindlmarket Winterland Wriggleyville (22)

Christkindlmarket is a traditional German style market that comes to the city around Christmas time. There's shopping, food and drinks from around the world and an all around cozy, festive atmosphere. Its the perfect place to get in the holiday spirit.

2:45pm drinks, lunch at Truluck's Seafood, Steak, and Crab House (23)

Great bar, delicious seafood, and super cool drinks, what more can you ask for? The shrimp was so good we were running and willing to fight for it.

5pm- BMO Magnificent Mile Lights Festival Parade (24)

I got to be in a parade! This one was epic, with tons of cool floats, music and dancing. If you're in the city around the holidays you have to see this.

8pm- Dinner at LH on 21 (25)

Restaurant on the 21st floor of the LondonHouse Chicago where I stayed. You can eat inside or outside and enjoy the amazing views. not only did I have a delicious meal, there were great vibes (a DJ was setting up). The drinks and dessert were great too.


8am- Breakfast at the hotel

9:30- Millineum park (26) , the bean (27), art gallery, walk around, shop.

1:45- Lunch at Lou Mitchell's (28)

Lou Mitchell's is a family Diner with great breakfast, brunch and lunch (I had chicken and waffles!). It is located near the start of route 66, and is the starting location of many people's journey along the road. They're also known for giving fresh donut holes to guests, boxes of milk duds, an orange slice & a prune, and a small cup of ice cream with every meal.

3:15- WNDR Museum (29)

wndr is an immersive art experience that is super fun to explore. Some call it a selfie museum, but I felt that it was more, because its not just pretty back drops but instead more creative art that is meant to be touched and played with. But yes, you will get cool pics.

5pm- Chicago Heli tour (30)

Helicopter ride over an amazing city, you cant miss! During the holidays you get to see the Christmas lights, which makes it even cooler.

6:45- Dinner Theater on the Lake (31)

9pm- 360 Chicago Observation Deck and TILT (32)

More views to end the night! 360 Chicago is an observation deck thats 1000 feet in the air and home of TILT, a ride that leans you forward on a platform so you can get unique views.


Breakfast, checkout, fly home.

Aaaaand, since more is more, here are extra things you could possibly do in the city:

(33) Navy Pier

(34) Shedd Aquarium

(35) The Field Museum

(36) Adler Planetarium

(37) Art Institute of Chicago

(38) Ice Skating Maggie Daley Park

(39) The 606

(40) Chicago Architecture Center (CAC)

(41) Lincoln Park Zoo, Brookfield zoo

(42) Chicago Theater

(43) Museum of Contemporary Art

(44) Art on the Mart

(45) I don't like sports, but apparently there are lots of sports things to see! Wrigley field and soldier field.

(46) Chicago Riverwalk

(47) Lincoln Park Conservatory.

(48) City Gallery in the Historic Water

(49) I know I already mentioned food, but pizza! and also so many cool bars, plus the music scene.

And last, and of course a great reason is:

(50) Because I might be there! I always find great deals out of their airport and its the perfect city for a layover!

So, see you in Chi town soon!

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