Chicago City Guide

I frequently get asked about Chicago and what to do when people visit. So finally, I have a post on the best places to stay, shop, eat, visit, caffeinate, drink and do! Stay up to date with my blog posts by signing up for my email updates here.

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John Hancock building shot by Jon.

My exact jacket is by my friend Christina. Shop it here.

What to do:

Architecture Tour – my favorite thing to recommend! I’ve gone on this three times and my kids love it too.

Museums – the easiest spot to go to 3 in one day: Adler Planetarium, Shedd Aquarium, and the Field Museum. My kids love all three!

Skydeck Chicago – I still haven’t been but hope to soon :). I just don’t want to wait in line.

360 Chicago Observation Deck – at the John Hancock building and known for the view! The photo above is of the John Hancock building.

Lincoln Park Zoo– free and my kids have been going here since they were babies!

Millenium Park (Cloudgate – the Bean) and Navy Pier – these two are super popular tourist destinations. In summer Grant Park (inside of Millenium) has tons of concerts and activities.

Rooftop bars – my favorite part of summer.

The Second City – I took my parents once and I LOVED it. Where many of the SNL casts have come from and I love comedy shows!

There is so much to do and eat, check out more below!

Where to shop:

The most popular spots have to be on Michigan Ave. So those are easy – just start at Nordstrom’s and continue down the path to Neiman Marcus and Topshop and Zara. There’s a variety of price points and you could spend two days just checking it all out!

Oak street and Rush street is where a ton of luxury brands are Dior, Louboutin, Barney’s, Chanel (hello new store and AMAZING). I’m also a big fan of Intermix  and Ikram. Ikram is like a museum of beautiful goodies and a must see even if out of the budget.

Where to dine during the day:

RL – The cutest spot by Ralph Lauren and a favorite of mine to take my guests!

3 Arts Club Café – So instagrammable and inside the huge Restoration Hardware in the gold coast. Must see and have the famous burger!

Au Cheval – voted the best burger – be ready for long lines or go during the week right when it opens!

Summer House Santa Monica – so pretty and feels just like you are in CA.

Barney’s – go to the terrace in the summer. A great spot when you are shopping by Oak or Rush.

Little Goat Diner – I go for brunch or lunch and a yummy Stephanie Izard gem.

Soho House – have the brunch/lunch or tea in the trendy West Loop spot under the pretty chandeliers. Also on Instagram quite a bit.

Chicago’s a huge food scene so there are a gazillion favorites but there are the ones I think are great for sit down and ones I go to often with girlfriends.

Where to dine at night:

See my post on romantic spots for date night! These restaurants are listed by price point and some of my ultimate favorites – I’ll probably do an update as things keep opening! But it’s a must flag post for you that love food. You can click on the photo below to go to the post.

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My red dress is linked here.

Where to caffeinate:

I wrote a full post sharing my top 10 coffee shops (that also happen to be Instagram worthy). Check it out here. I love a good coffee shop and these not only have great coffee but so cute for photos. Click below to go to the post.
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Where to stay:

Luxe stay and perfect spots for shopping:

Four Seasons Chicago (couples and family – the home alone pool!) I’ve stayed here many times and love the location and service. See a few photos of the room/view in this post here.

Langham Chicago – luxury and so instagrammable. The lobby is gorgeous, the service and rooms are beautiful. My favorite afternoon tea spot and recently had dinner at Travelle and it was so delicious. I’m doing a staycation at the end of this month there so stay tuned!

These two are my favorites for a luxe experience and there are a ton of hotels in Chicago but I consistently go to these two spots.

For affordable choices, I love the boutique feel of these three.

Thompson Hotel – great location as well and near all the restaurants. I’ve stayed here with my kiddos for the holidays!

Viceroy Hotel – haven’t stayed here but I love this hotel chain and the restaurant Somerset here is fantastic.

The Hoxton – in the West Loop and just opened literally this week (April 2019)! Love the decor and the rooftop bar/restaurant is so good.  I’m obsessed with Stephanie Izard’s food so I’m booking my reservation to eat at Cabra Civecheria ASAP.

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Outside of the Four Seasons Chicago close to Michigan Ave shopping. My green dress linked here.
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Where to take photos:

Check out my list of the best places to take photos here! So many great spots and one of my favorite posts about the city! Click below on the photo as well to go to the  post.

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Where to drink/go out:

It’s almost Summer! It’s time for rooftop season and these are my favorites. My full list of the best rooftop bars is here. A new add to this list is the Hoxton rooftop.  Click below to see the post as well.

I don’t go to “bars” that often and I dine out more so my list of where to go/drink are mostly the same as my suggestions in my restaurant post. Two additions would be The Aviary and Tao Chicago.

I hope this is helpful to many of you visiting and I love hearing from you if I missed anything you love in Chicago.  Happy visiting. xx


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