From The Congress Plaza To The W...We Fancy

When I was young I traveled with family and school, when I was in college I would travel alone or with friends even on a whim, and now with my husband, I am learning a new form of travel. As anyone that is in a long-term relationship knows, traveling with a partner must be a compromise. He doesn't want to do trivial sightseeing, she wants to take too many pictures, and everyone has a different idea of what is 'must do'.

For example, Will hates trying on clothes. Compromise: I didn't need anything so we only went shopping for him, which cut the shopping time by at least a third, and I only asked him to try on things that he liked. Well...other than the green pants. Surprisingly, he didn't pick those. Wonder why?

He's got skills, I tell ya. Just look at that ass...

I am happy to say that this trip was the first time that we were on the same page. We have learned to compromise, focus on each other, and most importantly- not stress ourselves out by over-planning. Very important on a ten day road trip, I must say.

I was very thankful for all the suggestions we got from friends, family, and bloggers as to what we should do in Chicago, and I'm happy to share what worked for us. I want everyone to have access to the secrets the city holds, and most importantly- I don't want anyone to be scared to go to Chicago! I can't tell you how many people tried to dissuade us from visiting, and I want to make sure that others can feel confident visiting this amazing city.

~To Do List Prior To A Trip To Chicago~

#1 Check the weather.

Chicago has extremes, and each season can bring problems. I knew that Spring and Summer were the best options, but we had to gamble on August due to our vacation schedule. I heard that there can be bad thunderstorms in August, but we had great weather up until the last day. However, if you do have bad weather, just embrace it. We went to Flattop Grill for the second time, Will offered to take me shopping again, and we visited Garrett Popcorn to get fresh made Chicago Style popcorn to feed my popcorn addiction.

#2 Check out local events.

Sites like Choose Chicago and MetroMix could give you insight that the average tourist won't have. For example, in the summertime they have fireworks at the Navy Pier every Wednesday, and Millennium Park has FREE concerts in a state of the art amphitheater.

#3 Purchase Discount Packages for the Main Attractions!

Sightseeing can get expensive, so don't pass up these deals. Through Smart Destinations you can buy a full pass or create your own pass to see the city at a discount. As I mentioned, we didn't want to over-plan, so we purchased the Skydeck, Navy Pier, and an Architectural Cruise for $55 a person. Not only did we save money, we also had instant access to tickets through our phones, and had flexibility to fit the attractions into our schedule with zero constraints. *If you are Military, check with the USO before you purchase because some things are already free! You can also visit the USO on the Navy Pier.

#4 Book Hotels in The Loop.

I kept hearing that it was such a "Big City" and hard to maneuver, so I took out the middle man and decided to stay in The Loop. It was more expensive than staying outside the city, but if you figure in the drive time and stress, then I think it's totally worth it.

We booked a deal through a travel site for The Congress Plaza Hotel, which was the cheapest and also had the cheapest parking rate at $39/night. I never thought I would be okay with $39 dollars a night for parking, but it was still better than the $100 that others charged. The Congress was an older hotel, but had loads of charm and was well maintained. It is directly across from the Buckingham Fountain, so it was the perfect location and had a great view. I actually couldn't believe that we could see the lake from our room.
Pretty badass. 

As sad as we were to leave that view, I had also looked into staying at the W Chicago. It is one of my favorite hotel chains, and since I usually stay there with work, Will had yet to experience it. At $300/night and $60 for parking it is pricey, but sometimes the splurge is totally worth it...But guess what? If you are Military or a member of a Travel Club, then you should definitely check for discounts. We were able to get HALF OFF for our last night in Chicago! That is simply unheard of, but I'll take it.

Just so you know, those lamps are taller than the first floor of the hotel. I realize that they could look like I just used a strange camera angle, but nope, they are that big!

Life isn't about finding yourself. It's about creating yourself.

So yes, it is expensive, but the Holiday Inn Express doesn't open every door for you, there are no granny smith apples and cocktails in the lobby, and there definitely isn't a full gym with touch screen tv's on every treadmill.

Let me tell ya, when you know you are about to eat Chicago Deep Dish Pizza, an extra workout in the gym seems like the best idea EVER. Then we were prepped and ready to round out our trip with a visit to Giordano's, which is arguably the best Deep Dish in town.

The one thing you need to know is that the pizza takes 45 minutes to cook. If you go in there starving you will not be a happy camper. Your best bet is to Pre-order online or Pre-order while you wait for a table. You could also order an appetizer to tide you over, but all I wanted was pizza, so there was no room in my stomach for anything but. All I can say, is that it is DEFINITELY worth the wait. So much so, that I ate myself into a food coma, and I would do it all over again.

To be honest, I could do Chicago all over again. There is so much more that the city has to offer, and I'd even be willing to knock this checklist out aaaaaall over again.

I think it's safe to say that we dominated Chicago and can officially cross it off the bucket list. With that being said, it also means that the vacation recaps have come to an end. I hope you found them enjoyable because I sure did, and thank you for following along.

Everyone have a Tiggerific weekend.

For more reading pleasure, read about our first day at the Skydeck, the second day seeing the city from a different persepective , and don't forget about our Reunion or our time in Ohio. Personally, I think they are enthralling ;)