#CTLTravels To: Chicago

Chicago travel guide

Chi-Town, The Windy City, City in a Garden, whatever you call Chicago, I call it the best city to visit over the holidays. While I had anticipated lots of wind and cooler weather, I did not realize that this city takes Thanksgiving and Christmas so seriously! Whether it was a conscious effort on the city's part, or just blind luck, I found that I left Chicago in the proper Christmas spirit thanks to the traditional decorations on every building, the Thanksgiving Day parade and the general glee on Chicagoans. 

I've been to Chicago a few times but always stayed in the 'burbs and never got a chance to really experience the city. AMH and I decided that we needed a long weekend getaway over Thanksgiving. Each time we started planning a weekend trip, Chicago was always at the top of the list but we pushed it aside so many times because of just how darn expensive the city is. How expensive you ask? Chicago makes NYC look downright affordable. Everything in The Loop (that's right downtown Chicago) hotels, food, transit, attractions, is a lot more expensive that most American cities and because we were visiting on a major holiday, we knew we were in for some out of this world prices. 

We knew we would only have 2-3 days here and wanted to see as much as possible in a short amount of time. To accomplish that, we would have to bite the bullet and stay right downtown. As soon as we started looking, and I watched the cost of hotels skyrocket, I thought we would have to put Chicago off again. Just when we were about to find another city to visit, an alert popped up from Expedia with a great deal on a boutique hotel. It was too good to pass up so we booked right away! Excitement gave way to a very grave feeling of "what have we just done!". 

Obviously everything worked out and I'm excited to launch a new travel series here on Celebrating This Life sharing all the details of our weekend in Chicago. I received so many questions about how we planned our trip, which I have broken down into a few headings; The Planning Process, How I Saved, Where I Splurged, The Hotel, Attractions, and What I Would Change. I hope you find this guide and layout informative and helpful for planning your next trip.

If you'd like to see more photos from my trip you can search out the hashtag #CTLTravels on Instagram

After booking our hotel and quickly Googling the top things to see and do in Chicago, we realized that there really is a lot we wanted to see and we were short on time. We had to pick which items would just have to wait for another trip and settle on a few items each that were non-negotiable. Because we were visiting over the holiday weekend we read up on what events were going on in the city from the Choose Chicago website.

The Christkindlmarket was the first thing I found that I wanted to do. Then AMH found the Skydeck in the Willis Tower (AKA the Sears Tower), we both agreed that we needed to eat at Frontera, Chef Rick Bayless's restaurant (remember this post where we followed him to Kentucky and got to meet him?) I also wanted to see The Bean, try my hand at skating, and do a little shopping on the Magnificent Mile. AMH added a visit to the John Hancock building, Shedd's Aquarium and since we are both art lovers, a visit to the Art Institute of Chicago.

It was a large list but we knew we could make it work, and also have some time to wander and see where the wind would take us. I also used the weeks leading up to the trip to search the #Chicago hashtag on Instagram to see what locals where up to. This is how we found some great photo ops and a few of the restaurants we ended up eating at!

I very smartly packed only sensible footwear knowing that we would spend the majority of our time walking, and I have to say I still came home with blisters! We packed the night before as lightly as possible (which for me still meant one carry on luggage and one overnight bag), loaded the car at 6 am and we headed for the Sarnia/Port Huron border. Flights out of Toronto are cost prohibitive and because I have a fairly new car, we knew we would only be looking at two tanks of gas.

A few years ago we bought Nexus passes for us and the boys. We are pre-screened and we get to use the border lanes designated for Nexus pass holders. It cuts down significantly on our wait time, which all eats into our vacation time. We made sure to have our ID along with print outs of our hotel reservations in case Customs at the border asked for them.

There were a few things that helped us save some money on this trip with the major one being that we opted to drive instead of fly (two tanks of gas less than $100 vs. two flights at $600 plus taxes and transportation to and from airports). It is eight hours from Kitchener to Chicago and we opted to use any and all toll roads to help speed up our travel time. We bought an EZPass more than 10 years ago which is connected to our credit card and automatically takes the toll fare from our transponder. No need to wait with cash at a tollbooth.

The first night we were in Chicago, we decided to visit the Willis Tower. Upon seeing that the wait time just to purchase tickets was two hours, we decided to leave. As we were doing that, a security guard filled us in on the City Pass. With this pass you get VIP admission to five top city attractions for $100 US. Just visiting two of the listed attractions would have cost us more than than $100 and with VIP status we got to use a separate entrance that had no line. For each attraction we visited, Willis Tower, John Hancock Building, Shedd Aquarium and the Art Institute of Chicago, we walked right in. Each attraction had a 1-2 hour wait time so this City Pass really saved us both time and money.

The other major way we saved was by booking our hotel through Expedia. We were able to get non-posted rates at a boutique hotel (more details on full cost below) and free parking. Now you might be thinking, who cares about free parking. Well, remember when I said Chicago is very expensive? Hotels charge $40-$50 a night for parking. So, getting parking for free for two nights meant we could use that extra $100 for something much more fun! We didn't know we were getting free parking until Expedia emailed us a few days before. We have used Expedia exclusively to book our family vacations since they launched in 2001. Because we are VIP members and the hotel we stayed at is a +VIP Access Hotel, they offered us this little perk. I have to say, it's been the little things like that that keeps us planning our vacations with Expedia!

A minor way we saved was to use Uber to get around when our feet had finally had enough. We took three Uber trips at a cost of $6 each and one subway ride at $12 for two single use tickets. Uber is much cheaper than any of the public transit or taxi options and because it's all handled through the app, there is no need to carry small bills with you.

Well...I bought myself a Gucci Soho Crossbody in Red, but I don't think that falls into the category of splurging on vacation. Although, whenever I do buy a luxury item I always time it with a trip to make it extra special!

Our biggest splurge had to be dinner at Frontera on Saturday night. We ordered appetizers, entrees, a bottle of wine, and dessert drinks which included a $20 glass of dessert tequila for AMH. The bill was large but it was incredibly worth it. The meal was fabulous and had been prepared by our favourite chef Rick Bayless. And we know that it was prepared by him because we saw him in the kitchen! As we walked to dinner we peeked in the window, the kitchen windows look out onto the street, and we saw Chef Bayless with this sous-chefs getting plates out. We made a reservation a week in advance and got the time we wanted, but I wouldn't have left it any later to make a reservation because this is a popular restaurant. Especially on the weekends.

Eating in Chicago had to be our greatest expense. There are a number of wonderful sit-down restaurants (re:pricy) and little to no fast food places. In fact, I only saw one McDonald's and other than a few Dunkin Donuts and Starbucks, we encountered no other fast-food establishments. As much as I did love getting a decent meal, it ate into our spending money quickly. Even our pizza lunch cost us $100! Granted, it was the greatest pizza I have ever eaten and I would definitely recommend visiting Pizzeria Uno, they are the birthplace of deep dish pizza!

We stayed at the ACME Hotel in the River North area (only 2 blocks from the Magnificent Mile!) It has a great hip, boutique hotel vibe. The rooms came equipped with Amazon's Alexa to give you information about the hotel and area and free hot coffee was delivered to our door each morning in a thermos. You can even borrow a guitar (equipped with earphones) and an Apple Watch to track all your steps! I loved that the rooms came with small bites, drinks (both alcoholic and non) for a small fee, including a make your own cocktail kit. Free Wi-Fi is always a big plus for me so I can use my phone and tablet while on vacation.

The hotel lobby was all decked out for the holidays, complete with ACME swag to bring home as gifts and a leg lamp al a A Christmas Story in the window. They also have a bakery/coffee shop and a restaurant bar on site.

I wanted to share exactly how much we paid for the room using Expedia. To book our room directly on the website is $249 US a night, below is what we paid and remember we stayed over the Thanksgiving long weekend.

Price breakdown
Room price C$309.34
2 nights: C$127.47 avg./night
23/11/2017 C$99.95
24/11/2017 C$154.98
Taxes & fees : C$54.41
Subtotal: C$309.34

A little over $300 Canadian compared to $500 US. That's a huge difference! Plus as I mentioned, getting the parking for free really saved us some money. Since we've been using Expedia for so many years we were able to cash in $25 dollars in points towards the final total.

Would I stay here again? Absolutely. The rooms were clean and comfortable. The staff friendly and helpful. The location can't be beat and neither can the price we were able to get from Expedia! 

Purchasing the City Pass really allowed us to visit a number of our 'must see' places. The VIP access meant that we didn't have to wait 1-2 hours in each line up to enter. We also were able to get little perks like a free 4-D movie was included with our ticket to Shedd's Aquarium. We used it to see a 15 minute 4-D movie of Rudolph that was cute and fun!

Our first night started at the Christkindlmarket, then we walked over the Chicago River and headed to see The Bean in Millennium Park. After snapping a few photos we walked to Buckingham Fountain (you might recognize it as the opening scene for Married...with Children). Back over the river and we ended up at Willis Tower to see the SkyDeck (this is where everyone takes those very popular photo ops). We stopped at the Chicago Theatre to see the famous Chicago sign before heading to dinner at Weber Grill Restaurant (yes it's a restaurant of the famous Weber BBQ's).

The next day was Black Friday so we headed out in search of bagels and coffee before a little shopping on the Magnificent Mile, which included a stop at Magnolia Cupcakes because who doesn't love a cupcake! After taking our purchases back to our car, we visited the John Hancock Observatory, which is now known as 360 Chicago. Here you get some amazing aerial views of Chicago and Lake Michigan. We stopped by The Drake Hotel to look around. We both have a hotel bucket list a mile long and this one has been on there for some time. It was lovely to see it all decorated for the holidays.

Our next destination was the Art Institute of Chicago. We were mostly interested in the Impressionist paintings and lucky they are all grouped together. We saw a number of Van Goghs (my fave), Monet, Renoir, Cezanne, Munch, and George Seurat’s A Sunday on La Grande Jatte, which 80's movie lovers will recognize as the pointillist painting from Ferris Bueller's Day Off.

After breaking for lunch we headed to The Field Museum which we were told would be closing in an hour. The only thing I wanted to see there was Sue the T-Rex, who is the most intact T-Rex in the world, and she happened to be displayed in the lobby. We opted to skip the museum and instead when to Shedd's Aquarium to see the beluga wales and the 4-D Rudolph movie. Then it was time for our dinner at Frontera which exceeded all expectations. And since we've been following the chef for more than 5 years, those expectations were very high!

We wanted to be on the road to leave Chicago by 9 am on Sunday. We were up and ready by 7 am, with a thermos of coffee provided by the hotel, and walked to the outdoor skating area and Christmas tree in Millennium Park. This is the perfect time of day to visit The Bean if you'd like to see it before the crowds fill in (and fill in they do!) We Uber'd back to the hotel to pack up and check out, which we did right at 9 am just as we had hoped.

Usually it takes a few days of reflection for me to decide what things we really should have skipped and what we should have done instead on vacation but this time, I knew right away.

Skip the Willis Tower. I had read it over and over in blogs, travel guides, tourism websites and even while searching out the #Chicago hashtag and I really regret not listening. The Willis Tower is where everyone is taking the selfies and photo ops in a glass bubble on the side of the building, 103 stories high. Now I know we were visiting the city on a holiday weekend so there were probably more people out playing tourist then normal, but here's how our experience worked.

Waited in line to purchase tickets, waited 30 minutes in the wrong line because there is zero signage (there was a group of us, it wasn't just me and AMH), got into the correct VIP line (remember when you have the CityPass you are supposed to bypass all lines) and waited 30 minutes for an elevator. Once on the 103 floor there are 4 SkyDeck pods which, you guessed it, each have a line. The wait time for each one was an hour. It was crowded and chaotic and those two things make my anxiety levels go through the roof. We both decided that it wasn't worth the photo op and we were pretty sour on how long we had waited so we made the decision to go see something else. And do you know what we found at the elevator? Another line! I kid you not. This one was another 30 minute wait.

By the time we got out of the building I needed a stiff cocktail. I should have listened to literally everyone who said it would be like that, but I thought to myself that it couldn't be that bad. It is worse (I've left out the annoying tourists with cameras that kept bumping into everyone, the children running amok or the not one but two families with strollers that ran over our feet). I do not handle chaos very well so I thought it was just me being sensitive but my always calm husband said it was a nightmare in there, so for him to say that you know it was really bad.

What we should have done instead was visit Navy Pier. It's a popular summer destination and equally so in winter. They have a large indoor activities area with skating, concerts are held here and you can take boat tours from here all year long.

If we had a little more time, I would have liked to take the train out to Winnetka (30 minute ride) to see the Home Alone house. Yes, I have seen it before on a previous trip but I was hoping to catch a glimpse of it all decked out for the holidays.

That's about it. We were pretty satisfied with our weekend away and other than the minor headache of visiting Willis Tower, I really wouldn't change a thing.

I'd love to hear from you! Do you find this layout easy to follow? Anything I am missing? Does this make you want to visit Chicago now ;) Let me know your thoughts in the comments below!

1 comment

  1. I live here and you probably did more than I have ever done! Sounds like you stayed in the BEST area and got to try so many great restaurants. My husband works in the Willis tower; after being there you can probably imagine how crazy that must get for him every day.

    I'm totally dying over your bag! I'm happy that you need to come back to do more things. That way I can see you next time!