Chicago – A Weekend in the Windy City

Chicago – A Weekend in the Windy City

Chicago – A Weekend in the Windy City

I found this quote and I felt that it described Chicago perfectly how I experienced it! Chicago is something out of this world! I know what you are thinking…CHICAGO??? Really?! Yes, really! I always wanted to go to Chicago just to go but never thought I would love it as much as I do now! It was something totally unexpected in the sense I thought it was just a knock off version of New York, but it was something much more. So the main thing that was very unexpected for me was the style and the architecture! There were definite hints of European influences in the designs and styles of the buildings. On some buildings and churches it really reminded me of the styles that you see in Italy and other European countries especially at the top of the buildings with gargoyles. While walking around I couldn’t help but feel like I was in another world…or country!

Also I am happy to announce that I will be doing a Travel Series focusing on mini vacation getaways! Sometimes we may not have the vacation time or money to go on a big elaborate vacation, but we would like to go on a vacation. A weekend vacation can be really fun and affordable. Be on the look out for more mini vacation ideas under the travel section of my blog here! I have 2 mini trips coming up soon!

“Going to Chicago was like going out of the World!”  ~ Muddy Waters


My husband and I did a couple’s trip to Chicago for the weekend! It was 4 couples total and one of the couples was from Chicago and so she was giving us a “Taste of Chicago”! We went in early September so the weather was great but we still needed a light sweater/jacket.  This was a weekend trip Saturday through Monday! Even though it was 3 days, we definitely got to see a lot. So if you are doing a weekend trip to Chicago, there are a few places I definitely recommend that you visit while in Chicago! For details on my outfit, check out this post!



On this trip, we booked our flights on Spirit Airlines! Yes, the beautiful low-cost airlines…lol. Before you skip over this part, let me explain to you how my FIRST spirit airlines experience on this trip went and a SECRET that Spirit does not advertise that some people do not know! So the key with flying with Spirit is to know what you are getting into. If you know your expectation upfront, your experience will be rather pleasant. As many of you may know, Spirit is nothing fancy! It you want Virgin America, Emirates or America Airlines comforts, then this is not for you! But if you just want to get to where you want to get to, cheap with no frills, then you will be fine flying with Spirit.

Our flight to Chicago (Saturday through Monday) was only $80.40 TOTAL for TWO PEOPLE NON-STOP ROUNDTRIP!!! Yes, tax included for two people total! The only way we and the other 3 couples who traveled with us got this deal, is my paying for it at the airport. Online ONE ticket cost $80 but if you go to the airport and pay for the ticket at the counter, the savings is ridiculous! Each ticket cost $40.20 with tax. The only downside is driving to the airport, but we live 2 minute from it so it was no problem. The deals are first come first serve and they only allow so many tickets for the price and they slowly increase it from there. Try to go to the airport during non peak hours. I went around 10pm so I was pretty much in and out.


TIPS: Bring your bag ahead of time to Spirit and test out the size. They will let you bring one small bag FREE. Anything that does not fit in there sizer, will get charged $55. They only allow one bag free and that includes a purse. So ladies be sure to test the size with your purse in it too. If it looks bulky at the gate, you will be in for a rude awakening and be charged a hefty fee.

Also refreshments are not included on the plane for fee. I suggest you by snacks at Walgreen and drinks after you go through security. You can always bring an empty water bottle or Starbucks cup and fill it with water at one of the restaurants too. Pack Crystal Light packets in your bag if you want something more than water such as tea or lemonade.



Courtesy of

The hotel we stayed in downtown Chicago I would totally recommend! It is within walking distance from everything and it’s in the heart of Downtown Chicago! We stayed at the Residence Inn Marriott Chicago Downtown/Loop ! The hotel had several levels and our room was pretty high up but I love being on a high level room floor!  Our room was a little suite. There was a full kitchen, living room area and then a king size bed!

The décor was very contemporary which I loved! The bathroom I really loved! Very bright and modern as well! I loved the fact they had a separate mini area with a plug and mirror so I could do my makeup and hair! Our room also included free buffet breakfast which included your typical continental breakfast like pasteries, fruit but it also hot items like eggs as well. When we return to Chicago, we definitely would like to stay here again.

king-studio-suite-kitchen            king-studio-suite-lv


So Chicago is known for the food! So we definitely ate at a several different places and some of which was a little on the outskirts, but if you know the area and not go a night then it will be ok. One of our first stops was Chicago’s Chicken & Waffles! Everyone has probably had chicken and waffles and if you have not, you should definitely try it! It is really a great combination together! A nice southern style brunch I like to call it! My very first time having chicken n waffles was surprisingly enough a few months before this trip. I live in Dallas, Texas so I am from the south and many people are surprised that I never had tried it. I definitely had to say that the chicken n waffles here was definitely better than what I had here in Dallas. It is not just eating waffles with friend chicken but it is the receipe on how you make each item! Usually you eat it with a special gravy and or syrup. But everyone’s gravy and syrup is not the same. Theirs was very good and it is a lot of food for your money. The best way to try it out is split a meal that comes with 2-3 waffles and al a carte the chicken!


Portillo’s!!! ITALIANO!!! When we told our friends that we were going to Chicago, one of the top spots to eat at was Portillos! They have a really good Italian beef sandwich! That sandwich was really that good! When you first go inside, you may be a bit confused like I was. It almost gave the effect of a mini food court than an actual restaurant! It is very informal meaning you just wait in line, order your food and wait for your number to be called.

It is open seating so you sat wherever you wanted. We pulled two tables together since we were 8 people! It is two levels and you can order anything from sandwiches to hot dogs to pasta! My husband being Italian loved the Italian beef sandwich! I was not hungry at the time but I did have a couple of bites of his sandwich!


For dinner, our friends made reservations at Joe’s Seafood Prime Steak & Stone Crab!!! Delicious!!! I love the atmosphere of the place! White linen, low lighting and jazz music – it was a perfect evening!! The service was great too! The price is a bit on the high end, but the quality of food was superb! I ordered the crab stuffed shrimp with 2 sides that you order al a carte! The sides are sharable for 2-3 people! We chose the mash potatoes and broccoli! It was very good! One of the other couples ordered the lobster tail which was big in size! I got to try a little bit of it and it was very good as well!



Lastly a must try while in Chicago is Chicago style pizza at Giordano’s! Chicago style pizza is deep dish…I mean really DEEP DISH pizza! It is so deep that it takes an hour to make it! I was not aware of that before coming so order appetizers if you m on an empty stomach or else it will be the longest wait ever!

We did not have breakfast that  so lunch as our first meal were starving! The pizza was good…resemble in taste like lasagna! It was different but good! Because this pizza is practically a pie, I suggest sharing a medium amongst friends or just order a small because it so thick and hearty.




Chicago has so many things that you can do! It is such a big city – you can never get bored! Click for discounts on things to do in Chicago!  One of the first things you have to do is visit the famous “Bean”! To your surprise it is not called The Bean, but it called Cloud Gate which was constructed artist Anish Kapoor between 2004-2006! Located in Millennium Park you must visit this masterpiece! I went to go see it but did not know how beautiful and interesting it actually is! It was packed with people when we went and wedding partying pictures in the area as well!

I think the best time to see it is in the morning when there is less people and not in the late afternoon! With less people, you will have cool photographs! After checking out “The Bean” go get your shopping on the Magnificent Mile! The famous Michigan Avenue is  where you can find all the shops, boutiques and restaurants. Michigan Avenue is quite a long street but you will be able to find everything there from designer brands HM, Zara and Forever 21! Since this is home of the Chicago Bull you will definitely be able to find all things Bulls and Michael Jordan!

Also you will be able to find the famous Garrett Popcorn! I heard of Garrett Popcorn and everyone told us to  buy some, and I am so glad I tried it out! It is a very good popcorn! I loved the caramel! That one was my favorite! Most people get the Garrett Mix which was a combination of caramel and cheese.



In the evening time definitely check out Navy Pier! The Chicago skyline at night is so beautiful! There is so much to do at the pier from restaurant, boat rides, live music and an enclosed Ferris wheel that is year round! favorite spot was The Signature Room! We did not make it to the Sears Tower, but I love rooftop bars! It was a bit windy that day so we opted for an indoor high level bar in the John Hancock Center building! The Signature Room (restaurant) is on the 95h floor while The Signature Lounge (bar) is on the 96th level.

It’s free to get in, but you have to order one drink – it does not have to be alcohol. The prices of the drinks were on the higher end around $16-17, but they were very good. The view from the Signature Room was AMAZING!!! I loved it so much! You are pretty high up so it may be a bit much for some but you can always ask for a table not near a window. But if you like a view try to get a table on the left side. The right side at night is not the greatest because of the water so it is just black. Forte sunset I am sure you would want the right side.



I definitely had a great time in Chicago and can’t wait to go back! If you been to Chicago, I would love to hear what you favorite places are! Leave a comment below! Thanks for reading and I hope you found this guide helpful!





  1. November 16, 2016 / 10:27 AM

    Wow! I can’t wait to visit Chicago! Thanks so much for sharing!

    • November 18, 2016 / 1:20 PM

      Thanks so much for the love!


    • November 18, 2016 / 1:19 PM

      You are very welcome! I’m glad you enjoyed it!


  2. November 17, 2016 / 12:17 PM

    Such a cool post!! Thanks for sharing . Chicago is on my travel list!!

    • November 18, 2016 / 1:19 PM

      Thanks so much for the sweet note!


    • November 18, 2016 / 1:19 PM

      Thanks so much! You will love Chicago! Such an awesome place

  3. Kristi
    November 17, 2016 / 8:49 PM

    Such an awesome post, with amazing tips and information!! Thanks so much for the post!!

  4. Ryan Roberts
    November 17, 2016 / 9:29 PM

    This looks awesome! Have been wanting to visit Chicago soon!!! Great tips!!

    • November 18, 2016 / 1:15 PM

      Thanks so much! You will love Chicago!


  5. November 17, 2016 / 9:34 PM

    Wow, so much fun! Chicago is one of my favorite places!

    Love all your tips! And $80 on two ticket?! That’s incredible! Oh, and when you go back, check out Gino’s East for deep dish, too. So, so good!

    • November 18, 2016 / 1:14 PM

      Thanks so much! Yes, it is such an awesome deal! I am looking for tickets for our next trip!


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