My Favorites in Chicago – A Travel Guide

I just got back from Chicago and I couldn’t wait to tell you all of my favorites in Chicago since I shared my favorites on 30a. You can read it here. First of all, Chicago has been one of my most loved cities since the first time I ever went in 1995.


April is really not the ideal time to go to Chicago.  We have gone in April because it coincides with a business trip for my husband. The ideal time to visit Chicago is in the summertime to early fall.  I did not get any pictures this last visit to Chicago.  These pictures are from when my son and I visited last August.

favorites in Chicago
Me and my son in Chicago at the roof top bar at the Ritz Carlton in Chicago last summer.

Places to Stay in Chicago

  • The Ritz Carlton – I have stayed here the last two times and it is defiantly one of my favorites in Chicago.  You really can’t go wrong with a Ritz Carlton.  The location is great and I love the rooftop bar.  Ask for a lake view room the view is spectacular.
  • The Four Seasons – It has been a while since I have stayed here but it’s a Four Seasons. Do I really need to say more?  The location is perfect for shopping and if you are there when the weather is bad the Four Seasons is connected to a shopping mall.
  • The Peninsula – I have only stayed here one time about 15 years ago.  It was wonderful. The one thing I remember about the room is the bathroom.  You could sit in the bathtub and watch television.
  • The Langham –  I stayed here once with my husband.  This hotel is beautiful.  I would not recommend staying here with anyone other than your significant other because of the bathrooms.  Even though there is an opaque wall between the bathtub and the bedroom you feel like the bathtub is in the bedroom.
  • Chicago Vacation Rentals – I have not stayed here but I am definitely going to be checking it out the next time I head to Chicago. They have accommodations from all the best providers including Airbnb, VRBO, Priceline and more at

Be sure to start making your dinner reservations at least a month in advance.  Some of these restaurants are very hard to get into.


  • RL Restaurant – This is by far one of my all-time favorites of Chicago!  Everything is delicious.
  • RPM Italian – We ate there for the first time last Saturday night.  It was so good.  All of the pasta is made in-house daily.  This will be first on our list the next visit along with their sister restaurant RPM Steak.
  • Girl & The Goat – This is one of my favorite restaurants ever!  The minute you know you are going to Chicago go ahead and make your reservations.


  • Quartino Ristorante – My husband and I stumbled onto this restaurant a few years ago while walking around.  They have a $25 Lunch Special for two that is one of our favorites.  If the weather is nice sit outside.


Snack Time

  • Garrett Popcorn – There may be a line but it is worth it.


Things To Do In Chicago

It really depends on the weather in Chicago on the things to do.  At least it does for me.  I do not like to be cold.

If the weather permits:

  • Architectural Boat Cruise – If I could only pick one thing to do this would be one of my favorites in Chicago.
  • Bike Ride – I love riding bikes here especially by the lake.
  • Cloud Gate – I thought this was called The Bean until I looked it up on the internet.  This is a great place to take a photo. This is also a great place to walk around.
  • Walk or Run by the lake – A great place to start is around Oak Street Beach or Navy Pier.
  • Lincoln Park– You could spend a whole day exploring this area.

Other things to do:

  • Bus Tour  – I learned so much about the city.  When I went the weather was beautiful and I was able to sit on top outside but if the weather isn’t good you could still enjoy this.
  • Shopping – Walking up and down Michigan Avenue you will find great shopping but don’t miss Oak Street.
  • John Hancock Building – This is one of the best views ever.
  • Art Institute of Chicago – A fun place to explore.
  • Shedd Aquarium – A great place to take the kids.

I haven’t had a chance to take the Segway Tour yet but I have heard it is so much fun.  We were going to do it this trip but it was too cold.

Have you been to Chicago?  What are your favorites in Chicago?

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