a winter weekend in chicago: 4-day itinerary (part two)

Hello lovies! As mentioned in part one of a winter weekend in chicago, I’ve recently had the opportunity to travel to and have returned from a 4-day weekend trip to none other than Chicago, Illinois. I’m so excited to share all the details with you, like what I packed,  where I stayed, and what I did in the Windy City.

My trip to Chicago was rather last minute and a tight squeeze into my schedule, but I made it work! I hopped aboard a Southwest flight early Saturday morning and departed on Tuesday afternoon.

I enjoyed cool temps (in the 20s), snow on the ground, and dressed sufficiently enough, disregarding my frozen fingers and toes. The gloves I brought were not very good and began to fall apart on day one.

Despite not sticking 100% to my itinerary, I had a good time and ate some great food. This is my weekend in Illinois!


saturday: day one

My weekend started out slow. I woke, finished packing, and was at the airport by 6:30 AM for my flight to Chicago. The flight went well and was on time for its 1 PM landing. It was 21 degrees when I landed, but as I was rather warm, the cool air felt nice.

I was picked up by those I flew out to meet (they had arrived Friday; I was unable to) and we drove a good 25 minutes to the hotel. Not too bad!

Hampton Inn & Suites Chicago Schaumburg

Hampton Inn is a branch of Hilton hotels and I’m always impressed with Hilton. They’re clean, quiet, staff is friendly, and I always get a good night’s rest.

Although, I wasn’t quite impressed with this one. The walls seemed a little thinner than I’ve experienced at other ones. It made it hard to sleep when I heard other’s televisions and conversations and every little thing going on outside the door.

Other than that, it was clean and the staff was kind and accomadating.

While I didn’t pick the hotel to stay at, it was conveniently located near shops and the freeway, but still a 30-45 minute drive to downtown. As I don’t drive, that equated to a 90-120 minute train ride or a $50 Uber/Lyft. This is greatly attributed as to why I didn’t get to do my full itinerary. I just wasn’t willing to sit on a train for two hours or fork out $50 everytime I wanted to go somewhere.

cost: $ to $$

Rating: 4 out of 5.

Cloud Gate

I really wanted to see this, so I was glad we got to! We drove downtown, walked around a bit, and then made our way to Cloud Gate. It’s quite big and truly the greatest of all mirrors. Like, I want it in my house. Is that possible? Anyone?!

I got a few pictures in and witnessed a wedding proposal (she said yes!) and saw two girls taking quincenera photos in the utmost beautiful dresses.

The view around was, as well, incredible as we were surround my all kinds of buildings, old and new.

cost: $free 

Rating: 5 out of 5.

Maggie Daley Park Ice Skating Ribbon

From there, we walked ~5 minutes down the street to the Ribbon. This was also something I really wanted to do, and I’m glad we went. I’ve grown up around hockey and can make my way (albeit very slowly) around a rink. I hadn’t skated in two years before then, so it was a real treat.

The Ribbon, though, was a lot smaller than I anticipated and, assuming because it was the weekend, was quite crowded, and the ice was rough. It wasn’t quite worth the $20 for me which was a bummer.

Nevertheless, I did enjoy myself and skated around a few times before calling it a night and getting some hot chocolate from their concession stand. They had a great variety of warm items available at reasonable costs.

cost: $5 or $20 with rental skates

Rating: 3 out of 5.

Chicago Prime Italian Restaurant

After skating, Chicago Prime Italian was recommended and several of us grabbed it to go. I’m always craving Italian. Literally. I ordered the spaghetti (with just marinara) and it came with garlic bread and a salad. 

One word? Heaven.

It is quite pricey, though, as my basic spaghetti was, well…there aren’t prices on the menu. But let me tell you how worth it that it was! I would – no joke – fly back to Chicago just to eat there again!

cost: $$ to $$$

Rating: 5 out of 5.

sunday: day two

This is where my itinerary went sideways. Perhaps I woke up on the wrong side of the bed. It started off with the people on the floor above running (like what even?) and ended with a really loud boom that I can only assume is that someone had fell or dropped something. It was odd. And the oddness just ensued.


I ordered my eggs wrong. I’ve never ordered eggs in my life so I googled the types of eggs and then when my food arrived, I realised I said the wrong thing. I meant to order over easy but instead asked for sunny side up. I giggle thinking about it because I was so confused as to why my eggs were raw-ish.

Despite my mistake, my food was delicious. I added hashbrowns and toast to my breakfast and topped it off with coffee I made in the hotel room.

cost: $$ (my meal costs $13)

Rating: 5 out of 5.

As I was waited to attend a hockey game that afternoon, more oddness ensued and – in respect to others’ privacy – it’s suffice to say we were unable to attend. As we didn’t go, I ended up not going to the Garfield Park Conservatory (free or donation) as I was going to catch an Uber from the ice rink to the conservatory (it would be significantly cheaper than form the hotel).

We stayed in and had Buffalo Wild Wings for dinner. I ordered the buffalo cauliflower wings and they were so spicy and so good! I’ve got to order them again!


monday: day three

Monday morning was slow going. I got ready for the day, unsure if I’d complete the day’s itinerary. I was pretty bummed about not going to the Conservatory the day before but was determined to not let it get me down. I thought perhaps I’d go that day instead except it was closed. So, I had to change plans and was left with a big question mark.

Corner Bakery

We ordered Corner Bakery to the hotel as it was close and I was craving pancakes. I grabbed the buttermilk pancakes with a side of scrambled eggs and made coffee at the hotel. Let me tell you. If you’re ever having breakfast cravings, specifically pancakes, Corner Bakery is the place.

I wish one existed here in Arizona. Or perhaps I need to fly to the nearest one, which is in Nevada.

cost: $$

Rating: 5 out of 5.

Chicago Pizza Authority

After brunch, rather than head downtown and rush through my itinerary, I decided to stay in and get to know everyone I travelled with and catch up with others. When night fell, I, of course, was craving Italian again. I ordered spaghetti and pizza from CPA.

It was so good. So good. 

Chicago knows how to do food. Hands down.

cost: $$ to $$$

Rating: 5 out of 5.

tuesday: day four

Happy last day! I didn’t get to bed until 2/2:30 AM and was utterly beat. I woke up and shoved whatever food I could find into my mouth and was barely able to take a shower. The weekend hit me and I stayed curled in bed until it was time to leave the hotel room and catch my flight back home.

O’Hare International Airport

I love when airports are simple and easy and O’Hare is simple and easy. We entered right outside of the check-in counters, dropped our bags off, walked a bit through security, and then emerged literally right where we needed to be.

There was a souvenior shop where I grabbed a glass for myself and a collectible spoon for my nunna. She collects spoons everywhere she’s gone and I started picking out spoons from my travel for her.

The food options were minimal. I believe Burger King was the only open place despite it being early afternoon. I was just thankful that they had an Impossible Whopper because I was starving.

Rating: 4 out of 5.

Southwest Airlines

When we travel for hockey, we travel with Southwest. They allow two bags on free and don’t charge oversized luggage fees. That’s great when you have a giant hockey bag and long sticks to match. I’m very neutral about Southwest. I’ve lost over $300 on a flight and couldn’t get that money back in any form but I’ve not had a bad flight with them. I do admittedly prefer to fly Delta but am not against saving money. 

As well, as someone with a severe nut and tree nut allergy that’s airborne, it’s incredibly reassuring and good to know that Southwest does not serve peanuts on board. (Note: this doesn’t stop people from bringing such aboard.) I’ve always been told to let the flight attendants know so they can make an announcement regarding no nuts, but I usually get shrugged off by Southwest flight attendants. (If you tell flight attendants on Delta, they make an announcement and will not serve nuts in any capacity.)

All in all, I was just happy to be back home and couldn’t wait to crawl into my own bed.

Rating: 5 out of 5.

finally home: phoenix sky harbor

Home at last! We landed at night and ubered home. I don’t remember what the temperature was, but it was most likely in the 50s. Can you imagine getting on a plane in 20F and landing in 50F? I was boiling! The temperature difference was crazy. I slept with the fan on high! It’s been a few days since I’ve home and the 50F weather we’re having this 40F to 70F winter we’re having is nothing. 

And, of course, in being home, I’m notorious for not unpacking. I sort of half unpack and then use my suitcase to collect literally whatever until I get annoyed that it’s out and shove it in the back of the closet. Does anyone else do this? No? Just me? Oops!

I’m really glad I got to travel to Chicago! While I’m unsure if I’d do it again any time soon, it was a nice place with great food and I definitely recommend it. Just stay downtown if your plans are there!

Until next time! Peace!

Hi, I’m Jade Madison!

When I am blogging, I work to bring you quality lifestyle and personal content, as well as printables to make your life easier.


Success! You're on the list.
check out this blog post
share this post:

more photos from chicago, illinois


new content every wednesday

Success! You're on the list.
clap to like this post:
share this post:
blogging | etsy | fashion | food | gift guides | life | travel | wellness

this post is categorized as: blog > travel > illinois

%d bloggers like this: