The Ultimate Chicago Travel Guide

WHERE WE STAYED

St. Jane Hotel

This hotel honestly exceeded my expectations.

Usually when you book a hotel online, the photos always make the place look much better than it actually is. In this case, the hotel was just as beautiful as it was in the photos!

I booked the room via the Hotel Tonight app (sidenote: if you’re not using this app to book your hotels, you are missing out! They have some awesome deals!).

The lobby was very modern and moody in the best way! The décor was very different from any other hotels I’ve stayed at previously. Gotta love it when hotels take the time think outside the box to create a unique experience.

Our room was just as gorgeous and unique, as you can see by the photos. The closet was probably one of my fave details. When you open it, it is all a pink marble. I mean, this closet is SO me and I need it in my home pronto!

Also gotta appreciate a gorgeous marble bathroom! I’ll definitely be using it as inspiration for when we get around to expanding the back of our home and adding another bathroom.

If I ever come back to Chicago, I don’t think I’ll be staying anywhere but the St Jane Hotel again. Beautiful décor, comfortable beds, perfect location from all the attractions, stunning view, and friendly staff. Doesn’t get better than that!

WHERE WE ATE

Giordano’s

Obviously we needed to try a deep dish pizza while in the windy city. I mean, how can you not?! We needed to know what the hype was all about! And it did not disappoint!
So much ooey-gooey goodness 🤤

We looked up what the best place is for deep dish pizza in the city, and Giordano’s was one of the top rated ones and around the corner from our hotel. So it was perfect for a late night meal after we checked into our room around midnight!

Cira Cafe

This mediterranean-inspired spot was picked purely based on décor 😆 #doitforthegram

We got to this spot a bit early, so since it was located inside a hotel, we just hung out in the hotel lobby for a few mins and just took all the cute décor in.

But despite choosing this spot based on the décor, the food here was quite delicious as well!

I also wanted to steal their blue latte mugs – they were so cute!

Cindy’s Rooftop

This is one of my highlights from the trip. If I could have spent more time here, I probably would because I am obsessed with the view from here! It overlooks all of Millenium Park, the Bean, and you can even see the beautiful boat marina. We got ourselves a drink and just took the view in. However, if you wanted a meal, you could do that too. But it was definitely quite a crowded spot, which I was expecting actually so I was mentally prepared for this.

Jojo’s Milk Bar

I’d compare this spot to like a Max Brenner’s here in Philadelphia. If you want a late night dessert, this is the place to go. The three of us shared a milkshake but there were plenty of other options do choose from.

Sunda

I don’t go to enough restaurants with asian cuisine (Charming is pretty picky when it comes to restaurants) so I was super excited that the girls I went on this trip with were just as adventurous as me and were down to try this restaurant. I enjoyed my meal SO much. But if you’re not a fan of tuna, be prepared because there’s a lot of items on the menu with tuna. I personally don’t like tuna (unless it’s tuna tartare) so options were limited for me. But the options that I did like were heavenly! I need to start going to more asian restaurants here in Philadelphia!

3 Arts Club 

(aka Restoration Hardware Cafe)

Oh the infamous RH cafe.

Are you even a blogger if you didn’t come here for brunch?!

It’s definitely one of those places that is over-hyped and is only worth it to enjoy the beautiful décor because the food was not anything special. Although it was quite nice to sit on soft, comfy seats with a delicious latte and enjoy the view. Especially since we stood outside (while it was drizzling) for 30 minutes before they opened up the restaurant. I wanted to make sure we get there early since this spot does not take reservations and I knew that there will be sooo many people trying to get in too. By the time it opened, we were 3rd in line to get in and there were probably 15 couples behind us. Once we were seated, I kept checking at the line and it legit never ended. I wondered how many other bloggers were also in the restaurant the entire time LOL.

Barrio

This mexican spot wasn’t the best of the best, but it certainly wasn’t the worst either. Just average, I guess. I ordered some tacos, which I thoroughly enjoyed!

Bang Bang Pies

I’ve never had a pie like the one I had here – SO GOOD!

It had more of a mousse/jello consistency and was so unique! I believe the flavor I had was raspberry lemonade but they also had some other unique flavors. Remembering this spot is making my mouth water now!

I loved how casual this spot was, not like any of the other places we tried. Which was nice to mix things up and go a different direction than I normally would.

London House Afternoon Tea

We had such high hopes for this place and were looking forward to ending our trip on a very high note here. Unfortunately this was the second largest disappointment from this trip (talking about the first down below). But that’s kinda of our fault because we didn’t really read any reviews.

We wanted a fancy afternoon tea spot to relax at the end of our trip. We also wanted to hang out on a rooftop (or a really really high floor of a building). So we thought this spot would kill two birds with one stone for us. Unfortunately, it didn’t kill any birds with any stone.

It was located on the 2nd floor of the hotel. Whoever designed this hotel and the way it operates, decided that the afternoon tea lounge should be located right next to where all the hotel guests check into the hotel. So we were drinking fancy tea next to the hotel lobby where people in their travel sweats and luggage sat a few feet away from us. Literally on the table next to us was a group of people NOT drinking tea but just waiting to check in. Plus, it was really loud since check-in time happens to be around the same time as afternoon tea hours. So it was not relaxing at all. I hate that this whole experience cost us $55 per person. Not relaxing and a waste of our money.

Gaslight Coffee Roasters

Located in Logan Square, this coffee shop was very hipster/grunge, which I didn’t mind since their latte was pretty decent if you like one that’s a bit more on the bitter end of the scale.

Free Rein Cafe

This cafe was right outside of our hotel, which was awesome and super convenient. We needed lots of coffee to energize ourselves for days of exploring and walking around. If you like a more milky and less bitter latte, this was a good spot. Super cute too and more up my alley!

WHAT WE DID

Field Museum

We made the mistake of walking allll the way to this museum from our hotel. I wish we took an uber or biked over to here for several reasons. One, it was a faaar walk. Two, it was a hot day, nothing was windy about this windy city that day lol. Three, this was on our first day of exploring the city and there were some major blisters involved after this faaar walk. Regardless of all this though, I’m actually glad we came here. It was such a beautiful spot and made me want to set up a picnic on the steps of the museum – such a stunning view from there!

Bike Ride

After walking all the way to the Field Museum, our feet were so dead. So we decided to rent bikes and ride all the way up the park up to the infamous Bean. It was a good way to get around the park and wasn’t as exhausting as walking in the heat.

Cloud Gate

This is where the infamous Bean is. Truth be told, I didn’t think it would be as special of an attraction. But it took me by surprise actually. It was gigantic! Plus, how can you not see the Bean when visiting Chicago?!

Riverwalk

This was one of my fave things that we did and no matter how many times we walked the Riverwalk, it wasn’t enough for me. Being the city-lover that I am, this gave me quite a high! It was just so stunning to see all the skyscraper views and seeing the gorgeous concrete jungle.

Lincoln Park Conservatory

Despite how hot and humid it was inside this greenhouse, it was so magical!

Ever since, I’ve been so inspired to be more of a plant lady but my thumb is just not green enough!

Lincoln Park Shopping

I love the small town feel of this neighborhood, despite it being really close to all the hustle and bustle. So many cute little shops to explore and get inspired by. I wish it wasn’t raining that day so we could have enjoyed this street a little bit more.

North Avenue Beach

This was the biggest disappointment from this trip. For one, it was raining that day so that definitely put a damper on our day. However, even if there was no rain, I wouldn’t really spend my day there. It was kind of trashy, to be honest. There were tents set up by vendors and they just made this spot feel kind of like the city didn’t care how the beach looked but just wanted vendors there to make money. The beach was stuffed with people though! Which clearly means it’s a popular spot in the city so why not put extra effort to make the “boardwalk” portion of the beach cuter.

Also, we made reservations for a daybed at the shore club, but we regretted it so bad. We thought it would be a cute place to just lay out, tan, and relax. Instead, it looked like a spot where trashy guys hung out just to party and pick up girls. So not our scene.

The customer service was also TERRIBLE for the shore club. There was no staff to be found and getting someone on the phone was awful. It was just an overall downer on our trip. But, again, we should have read reviews for this place, which we did not do so it’s kind of our fault for booking it.

Second City Comedy Club

Now this was 100% a highlight on our trip. We saw the Algorithm Nation show and it was HILARIOUS! It was unlike any other comedy show I’ve seen before, so I loved the new experience. Highly recommend checking out a comedy club whenever you’re visiting a new city, it’s always been a hit event to book for a fun evening.

Logan Square

This was a fun little area to stroll through. If you’re from Philly, I’d compare it to a larger Fishtown but not as established yet. Regardless, it has cute shops to explore, coffee shops, little restaurants, and a park right in the center.

TRANSPORTATION

We made our way around town on the subway and bus actually. They have an awesome transportation system there! Normally I probably would have just used an uber to get around town. But my cousin suggested that we use their public transportation system and I’m so glad we did! It was much cheaper than ubers too, we spent $20 on a 3-day pass and it was perfect for us! At one point, we did take a Lyft ride from the beach back to our hotel and it was the WORST Lyft ride of my life!

CONCLUSION