Your Guide To…Chicago!

7 Jan

The second installment of Your Guide To…

I recently hit the windy city (and oh yes, it was windy!) for new years this past weekend. You may be wondering why the heck I decided to go somewhere cold in the middle of winter, but I have been wanting to go to Chi-town for some time now. Even though the weather was chilly we still had a blast. Here are some cool places to check out next time you are in Chicago!


Oh my, oh my! The food scene was delicious. We had Googled some of the best restaurants in Chicago and made resos in advance, which I highly recommend. Here were some of our faves:

The Purple Pig


I’m not sure why, but apparently this place is famous in Chicago. This Mediterranean gem is right downtown and always has a solid wait time. You can’t make reservations so it may be worth you while to stop in and get on the list and then go shopping or to the Navy Pier nearby. We ordered a few things between 3 of us, including calamari, cured meat/cheese sticks, some sort of super tasty cauliflower, and a meatball. It was really delicious, and there were a lot of other items on the menu that looked like they would have been as well. A great spot, whether you stop for lunch or dinner.



This place was recommended to me and I’m so glad we went! It seems like a typical American-style restaurant but the food was much better than you would expect for such a place. The menu had everything from sushi to nachos to burgers to tacos! You would think everything would just be average when there’s such a large array to choose from but not here. We shared salmon sushi, chicken jalapeno tacos, and guacamole. Everything was FAB – especially the sushi! Our waitress was so awesome we asked her to come out and party with us girls (she politely declined but brought us a free dessert). Highly recommend for dinner!

RPM Italian or RPM Steak


These RPM restaurants are co-owned by Giulia Rancic, a TV celeb, so we kinda had to go :). RPM Steak was great…very comparable to your local steakhouse. We didn’t end up going to RPM Italian but I’ve heard really good things.



Oh my gosh you guys this is my newest fave for Italian food!! If you haven’t heard of Eataly before, it’s basically a really large two-storey shop for all things Italian (think pasta, sauce, truffles, plates, etc.) and has mini-restaurants in between – one for pizza, one for pasta, one for fish, one for…you get the idea. We chose the pasta one, but the menu is everything from pizza to pasta to apps. We again shared (we love to share!) a bufala mozzarella ball with salt, cherry tomatoes and basil, prosciutto/ricotta/sweet potato ravioli, and a meal/cheese platter. The bufala mozz ball may have been one of the most delicious things I have ever tasted. Like so good that I actually Googled where to get that at an Italian place in Toronto… We went here for lunch which is likely your best bet unless you have a reso. I’ve heard other Eataly’s in other cities are crazy popular as well…I now know why 🙂

Siena Tavern


Siena Tavern is another Italian spot (can you tell we love our Italian?), and very similar to HUB51 in atmosphere. They have a great brunch menu too. We went for brunch/lunch and everything we ordered was excellent! This place is also very centrally located in the west loop…basically where you want to be. Also a spot the Chicago Blackhawks frequent…if that interest you ladies.

Lou Malnati’s


Chicago deep dish pizza is infamous. And for good reason. We spent dinner on New Years Eve on our hotel room floor indulging in some deep dish delivery, and man was it good! Greasy and fattening, but very very worth it. Lou’s is a classic go-to for pizza in Chicago. And no need to order a lot – 2 pieces of the deep dish will be more than enough!

Garrett’s Popcorn


Another mainstay in Chicago is their Chicago mix, aka Garrett’s popcorn. You can literally smell the goodness across the street. It seeps out of this place and pulls you right in. We got a small bag to share between 3 of us (remember, everything is bigger in America), and it was more than enough. The Chicago mix is a cross between caramel corn and cheesey popcorn. Thanks a lot, now my mouth is watering.


Millennium Park

A no-brainer. You can’t go to Chicago and not check out the infamous Bean. I’m not exactly sure of the history behind The Bean, but it is an interesting piece of architecture that has quickly become a landmark in the windy city. In the summer there are great activities to take part in (like yoga – OHMMM). For you Instagrammers – a great photo op! Oh, and the rest of the park is beautiful as well.

Bears Game


Make sure to check out a Chicago Bears game if there is one. The stadium isn’t too far out of the way, and a football game is always a good idea. Ladies – don’t forget about the NFL purse rule. Purses cannot be larger than 4.5″x6.5″ to enter the stadium (think clutch size).

Chicago Blackhawks Game


My oh my, do Chicago-ians love their hockey! Blackhawks nation has taken over the city! The Hawks usually sell out, so if you don’t buy your tickets well in advance you may have to purchase from a scalper. Just make sure to go to one in a vest – they are registered scalpers.

The Navy Pier


The pier was great in the winter (a little cold, but what can you do) but would have been SO much better in the summer! There were a ton of bars and restaurants with patios and even a beer garden along the pier. The sights of the city, especially at night with the ferris wheel would be awesome. There is a free shuttle from the Magnificent Mile to and from the pier, so hop on that if you are too tired to make the walk out.

Willis Tower and John Hancock Tower


These two towers are located in different parts of the city but both offer great views. Be sure to go early to avoid long lines (there was a two hour line-up when we went to the Willis Tower) and make sure it’s a clear day. A cloudy one won’t do you any good.

Michael Jordan Statue


We never made it here this trip, but if you attend a Bulls or Blackhawks game be sure to stop by the MJ statue at the United Centre on your way in for a quick photo op!

Dylan’s Candy Bar


Only the biggest and best candy store ever, located along the Magnificent Mile. Founded by Ralph Lauren’s daughter (Dylan..duh), you will literally be “a kid in a candy store” here. It’s worth it just to take a peek inside, even if you don’t want to buy anything.

River Boat Cruise


Again, if you go in the summer, this is something you will definitely want to do! Whether your river boat cruise is a dinner cruise or just a tour, the views from the river are apparently amazing. It’s also a great way to get to know the city!


3 Dots and a Dash

3 dots

This super cute bar is kind of hidden away down a dark alley…a little creepy at first. But once you get inside it is a Hawaiian-style gem! They only serve custom cocktails, and you can get them in giant fishbowls to share. The wait times for tables are a little long (unless you go right at 5pm when they open), but there is standing room around the bar. A great spot for a pre-dinner drink or a nightcap.

Howl at the Moon Dueling Piano Bar


My favourite bar. Maybe ever (minus anything in Nashville). This bar features a few pianos, drums, guitars, and tamborines, along with pretty decent vocal abilities. The band members switch between all instruments and singing, and take requests. The songs are all upbeat and popular – a super fun bar if you are looking to just catch a live act and dance the night away! We went here two nights in a row!

Andy’s Jazz Hall


You can’t go to Chi-town and not take in some jazz! We heard great things about Andy’s and it was right down the street from Howl at the Moon. It is a typical jazz show, complete with tables for 2 in front of the stage dressed in white table linens. If you are looking for a more low-key night this is a great spot for you. Be sure to ask at the front when the band starts and finishes their sets so you don’t pay cover for a 10 min. performance.

Trump Tower or Roof at The Wit


We didn’t get to go to the top of the Trump or the Roof at the Wit because it was winter, but apparently these terraces are beautiful in the summer months. Just be prepared to pay for an overpriced cocktail or two. It is the Trump after all!

Public House


We went to this bar/pub on New Years Eve. It was great – dressed up because it was new years, but seems like it would be a great spot to grab a few beers on any night. There was a large dance floor and they had a lot of different beers on tap. If you are looking to mingle but want something more casual than a club, this is a great spot.



Untitled is literally that – there isn’t a sign out front. You will know it’s Untitled though because there will always be a line! We didn’t make it inside, but heard this Speakeasy-type bar is a lot of fun. Something to check out if you are in the area (west loop).


The Magnificent Mile








This wouldn’t be a blog post without information on shopping! The best shopping in Chicago is literally right along the Magnificent Mile, the main street (actually called Michigan Ave.). There are cool one of a kind shops, as well as your typical department stores…you can literally find everything you need along here. Happy shopping!

Well there you have it…hopefully this inspires you to take a trip to the windy city (in the summer of course:))



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