Where to Stay, Eat and Drink in Chicago

When I heard we were on our way back to Chicago in December, I was thrilled! We were going to a friend’s wedding the Saturday before New Year’s Eve. That left us with a day and a half to explore the wonderful city. I already experienced Chicago previously in the summer and it was such an enjoyable time. We were able to walk around, eat, drink, take pictures and experience a boat tour of the astounding architecture of the city. Chicago is a such an instagrammable city in the summer. Now we had another chance to experience this lively city but from a different perspective; the winter. I was a little weary of the cold weather everyone talked so much about, but the cold was definitely not going to stop the Wandering Queen from exploring the city! In this post, I have included my husband and I’s itinerary including our activities, the places we wine and dined, and the hotels we stayed at (for free) in the windy city of Chicago. If you are looking to do Chicago on a budget make sure to check out Em’s on The Road Blog post! She has great suggestions.

Map:

Where to stay:

Park Hyatt

We stayed at the Park Hyatt for two nights on our trip during the summer of 2016. Jameson and I used our Chase Hyatt Credit Card free night awards. Unfortunately, the free night awards are not part of the program anymore. Now, the credit card company only offers sign up points, but it can be used to redeem the Park Hyatt Hotel which goes approximately 25,000 points per night. You can also transfer your Chase Ultimate Reward Points to Hyatt if you happen to be low on Hyatt points. Staying at the Hyatt was a lovely experience because it was our first five-star hotel redemption using a credit card. At the time, it was the fanciest hotel we had stayed at. We were in complete awe. The hotel has a posh, luxurious, edgy yet traditional feel. Aside from the aesthetics of the hotel, the location was in a fantastic area! Being about 250 feet from the best retail in Chicago on Michigan Avenue, is always a huge plus. But, not so much for our bank account.

The Gwen

This time around, we stayed at The Gwen Hotel. We used our Starwood Preferred Guest Points to book one night, which at the time cost approximately 12,000 points a night. The Gwen was an enjoyable hotel. It was not as upscale as the park Hyatt, but the environment was elegant yet cozy. Inside, the hotel had a spacious bar which seemed to be constantly busy. Due to the crazy winter weather, we were not able to take advantage of their outdoor rooftop bar but it is worth keeping in mind for summer trips. The bar offered some yummy warm drinks which hit the spot after exploring the city all day in the cold.  The atmosphere was ambient but warm at the same time.

Where to eat:

Lou Malnatis’

If you are like me and love to eat and drink in a new city, then this next section is for you! We walked over from The Gwen to Lou Malnatis’ restaurant for lunch and were seated right away in the warm, homey restaurant. Jameson and I ordered some cold beers and a delicious deep-dish pizza. This was an exciting moment for me because this was my first time eating a Chicago deep dish pizza! The pizza resembles a layered pie with meat and cheese toppings. The pie (or casserole) was heavenly, warm and cheesy; perfect for a cold day. The restaurant was packed with bustling people enjoying the end of 2017. The warmth, the atmosphere and the tasty food made it the perfect place to spend the last afternoon of the year.

Eataly

Eataly was recommended to us by our friend that grew up in Chicago. The bottom area resembles a grocery store where you can buy, meats, pasta, olive oils, wines and fine foods. Upstairs resembles a farmers market, where you can dine in. We ate, drank, talked, and relaxed for a few hours in the unique market. I loved Eataly. I really wish they had one in Dallas. I would be shopping, eating, and drinking there all the time!

RL Restaurant

If you prefer an up-scale, fancy dinner, then RL restaurant is a perfect place for you! We first stumbled across this restaurant on our first visit to Chicago. One of the nights we stayed at the Park Hyatt, we wanted some after hour drinks and found the RL Grill (owned by Ralph Lauren) across the street from the hotel. We walked into the restaurant a bit later, around 10:30 pm, and it was packed. Only a couple seats were available in the bar area. We proceeded to get a small table and ordered some cocktails and escargot. It was decided, if we were ever in Chicago again, we would make our way back to this fabulous restaurant. A year later we found out that we would be back in Chi-town for New Years Eve, so I quickly made reservations. We were excited that we could enjoy our last meal of 2017 in this elegant restaurant. The food was wonderful (especially the escargot) and we left the restaurant ready to take on 2018.

Copper Fox GastroPub

After a New Years night full of dancing and livations, Jameson and I decided we needed food desperately, but, it was a bit difficult finding restaurants which were open on New Years day. Luckily, we found this cute chic brunch spot to eat. Once we arrived, only breakfast was being served. Jameson ordered eggs Benedict and I ordered Avocado toast with some honey butter biscuits. The food was delicious and filling which helped us through our last bit of wandering.

What to do

Michigan Avenue

Michigan Avenue has a copious number of well known shops. Even though I don’t like shopping when I travel, I loved walking down Michigan Avenue. Seeing all the different stores, entertainers (mostly in the summer months), and bustling people makes for an entertaining time. My favorite building on the strip is the Burberry building. I love how they implemented their staple design, to the look of their building.

The water tower (below) by the Park Hyatt looked enchanting, especially with the snow and Christmas lights!

The Bean

“How can we go to Chicago and not see The Bean?” I argued with my husband. Even though I had already seen the Bean on my previous visit, I wanted to see it again. I was also hoping that the Bean would have snow on top of it. His mom’s side of the family is from Chicago so he has seen it numerous times. Because of the 5 degree Fahrenheit weather, he wanted to skip out on my Bean visit. Finally, he reluctantly agreed to go and so, we took off, walking in the blistering cold. Trekking through the windy, cold conditions was miserable at times, but I loved being able to see the Bean once more. There is something so majestic about the Bean that seems to attract people to this wonderful structure. It was all worth it.

The Drake Hotel

Now I know that this is the section of “What to do” and I listed a hotel, but hear me out. If you are ever in Chicago on New Years Eve, you need to check out the Drake Hotel New Years Eve Party. We bought the VIP tickets to the event in August and I am so glad we did! My husband and I ended up dancing all night long and the DJ was superb. I highly suggest spending the extra money and get the VIP tickets because the VIP area was less crowded, better crowd, superior sound, and had jamming music. If we had bought the general tickets, I don’t think we would have enjoyed the party as much. We briefly went to the general admission areas and quickly retreated back the VIP area.

In the end, I loved visiting Chicago in the summer and the winter. But, if I had to pick the best time to visit, summer would take the crown. The piercing cold was a bit too harsh for us warm blooded Texans; although, I did enjoy this lovely winter wonderland. Have you ever been to a place in the winter and summer and noticed differences?