Travel Guide – Chicago

Travel Guide – Chicago

I went to Chicago over Easter and I think it’s safe to say this city stole my heart! It is such a vibrant city full of delicious food, fantastic bars, gorgeous gorgeous architecture and such fun sights to see. If you haven’t had the chance to visit Chi Town yet I highly recommend you do! Below I am sharing my top tips on things to do and see there.


1: Architectural Boat Tour

There are several companies that do these boat tours so you will have no trouble finding one. Ours took about 90 minutes, and we did it on the first day which I definitely recommend. It gives you a good sense of the city and then you know what’s what. It is so so interesting to learn about Chicago and how it all started. The architecture is some of the most beautiful Iv’e seen and its fascinating to learn the history of these buildings. I love how they are a mix of old and new, it gives such an interesting feel to the city. Besides learning some very fascinating information its an opportunity to take some great pics and you can do all these with a drink in hand (yes there is a bar on board) just make sure you go with a company that offers this.




2: John Hancock Tower

I had heard reviews from several people telling us to go up the John Hancock Tower but I also had heard of several other room top bars so I must admit it was hard to choose just one. However I am so glad we went with the John Hancock, no it wasn’t an outdoor venue so if that’s what you’re looking for maybe choose one of the other ones but it sure was one heck of a view!! We went up just before sunset and had a drink in the cocktail lounge. It is 96 stories high. We sat for a good while and took in the view as the sun set over Chicago, with a dirty martini in hand. HOT TIP: The BEST view in the whole place is in the ladies bathroom so be sure to sneak in there for some great pics (yes I did hold up the whole line by doing this, as did most other ladies) haha! Sorry Gents, no view for you! There is also a restaurant up there if you prefer to stay for a meal, but bookings would be required.

If you are extra daring you can go to the 94th floor and do the 360 degree observation deck, apparently an enclosed glass platform literally tilts outwards over Michigan Avenue. Try it if you dare.

There is pretty large lines to get up so allow yourself plenty of time for the visit!



3: Live Jazz Music

I wouldn’t call my self a die hard jazz fan or anything but after going to New Orleans and listening so some phenomenal live Jazz, I was happy to hear Chicago was also famous for some live music. There are several places around the city to sit back and relax with a cocktail and take in some tunes. We decided on Andy’s Jazz Club. They have a few sets per night and we stayed for some pre dinner drinks and really enjoyed the musicians we heard. There is something about Jazz that makes you feel super sophisticated isn’t there?!

4: Food

Where to begin?? Chicago is BURSTING with so many amazing restaurants, I will be here for ages if I go on about them all.

Firstly you should definitely experience an incredible steak dinner while in Chi Town. We had recommendations that Bavette’s was one of the beast steakhouses, but we tried to book about a month out and couldn’t get a reservation so if you are planning on going book as far out as you can! We ended up at Michael Jordan’s Steakhouse which was good, I enjoyed my meal but it wasn’t great.

Brunch – If you are a girly girl like me and love good food, good Rosé, insta worthy scenery and live music you MUST get to Hampton Social. You have probably seen it on social media before – That famous Yes Way Rosé sign?! It is even more fantastic in person.


We reserved a table ahead of time which I would advise especially on weekends. We went for brunch around midday and that was the perfect time, as we still had the brunch menu which has a lot of good breakfast or lunch options on it. I wasn’t expecting everything to be as wonderful as it was but I honestly couldn’t fault this place. We were lucky enough to get seated in the PERFECT area right under the famous wall, it was a beautiful sunny day, the breeze was blowing and the windows were open. We started of with a Frozen Rosé which was so yummy and got us nice and merry. We then enjoyed a lobster roll and it was so so yummy. It was very hard to choose as the entire menu looked amaze and I wanted it all. And I washed this all down with another cocktail, a tequila based one which was HOT PINK, I mean what’s not to love!?!



The service here was flawless, staff super friendly and we honestly had such a wonderful experience. It’s the perfect place to relax for a long leisurely lunch and feel like you’re in the Hamptons.


Eataly – If you have never been to an Eataly you should absolutely get to one. I have now been to the NYC one and Chicago. So amazing. There is a selection of Italian vendors and restaurants. You can either buy food to take home and cook yourself or you can eat at one of the many many places inside. Too many goodies to name but my absolute favourite thing to have there is the meat and cheese charcuterie board, accompanied by a glass of Presecco. So simple yet so fantastic. I was in heaven! Hot tip: Try the fresh mozzarella! HOLYYYY!



Deep Dish Pizza – If you haven’t done it before, you need to at least once in your life and Chicago is definitely the place to do it. I’m not going to lie, its INTENSE! Definitely a tourist thing. Two slices and you need a nap haha. But it’s yummy and fun to do. Don’t go to a chain restaurant try to shop around for more authentic ones.

5: Must See Sights

“The Bean” –  No intro needed, I think we have all seen pictures of The Bean at Millennium Park. Its a HUGE tourist attraction so you need to pick your time to visit. It was super super busy the day we went as you will see from my pictures below. But still a lot of fun. Its right in the city on Michigan Avenue and you get awesome reflections of the gorgeous Chicago skyline in “The Bean”. The park it is situated in is so beautiful with lots of shady trees you can sit under and relax with a good book or picnic. I loved paying a visit here was lots of fun.




Lincoln Park Zoo – This is great especially if you have kiddies. It’s free to get into and there are some gorgeous animals there. I was surprised with the size of the zoo actually given that it is free. My highlights were the Flamingos (because who doesn’t love these beauties), the penguins, and the leopards. If you have some extra time on your hands and it’s nice weather I definitely recommend a visit here.


Museums – If you want to catch up on some history and knowledge this is a good way to spend a few hours. We went to the History Museum which was interesting to learn about some background of this gorgeous City and they had a really fun fashion exhibit at the time we went which of course I loved. However I know there are several other museums that would be worth a visit also.

Art Institute of Chicago

Museum of Contemporary Art Chicago

Field Museum of Natural History

Museum of Contemporary Photography

The list goes on, there are SO many museums so I’m sure you will find one to suit your interests.

Navy Pier – This would again me a good activity if you have kids. It wasn’t summer when we visited so a lot of the vendors were closed. It’s no Santa Monica Pier but still fun for a visit. We walked to the end of the Pier and the view was gorgeous, looking over the water with Chicago behind you. We also rode the SkyWheel which is HUGE. Again, amazing views from a birdseye level. The water was clear and so blue and the city skyline looked phenomenal. And for those of you that are a little afraid of heights like me don’t worry the pods on the skywheel are enclosed so you feel nice and safe!


River Walk – You can’t miss it. Right downtown the water runs right through the city and is lined by the stunning architectural designs. They have such a wonderful concept with specific paths as well as seating so you can walk along the water and admire the views, or sit and enjoy some down time. There is also a selection of restaurants down there if you want to stay a bit longer. Definitely worth a stroll along this beauty!




Magnificent Mile  – I mean, you can’t really miss it. If you want to shop till you drop this is the place to do it! An endless strip of shops, this is the place to me. Also such a pretty street its so lovely to walk along, flowers blooming everywhere and the hustle and bustle of the city life. You could do some serious damage on the credit card here!

Willis Tower – We didn’t actually make it up there because the line that weekend was INSANE. But similar to the John Hancock tower you can get insane views of the city so if this is a good option if you decide not to go to JH.

6: Accommodation 

We stayed at The Hyatt Regency and it was the PERFECT location! It was overlooking the water which was gorgeous, had wonderful amenities in the hotel including a fresh food market you could grab starbucks from, or quick bites. It was literally steps off the Magnificent Mile where you have everything at your finger tips. Boat tour starting point, shops, restaurants, bars, stunning buildings and so much more. I can’t recommend this hotel and location enough. Staff were very friendly and if you like to live the city and be close to all amenities and attractions this is ideal, I would absolutely stay here if I go back to Chicago. OH and very important to note – their room service breakfast is EVERYTHING!! Seriously best tasting room service goodies I have ever experienced! Because I mean who doesn’t absolutely adore breakfast in bed!! Necessity!



I would love to hear your travel stories. Have you visited Chicago before? What were your favourite things to do or see?

Happy Travelling!










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