Chicago Trip Report

A couple of weeks ago Tom and I took a quick trip to Chicago, one of our favorite places to visit. It was our first time back since Covid and it was an especially enjoyable trip.

We had the most incredible weather – sunny and warm the whole time. We ate/had drinks outside a number of times, which was completely unexpected for late October in Chicago.

The trees were at their peak and the leaves fell on us all weekend as we walked around the city. It felt like being in a movie.

We did some new to us things, like exploring the University of Chicago campus, and some old favorites, like shopping at P.O.S.H. (okay, that’s just my favorite) and taking the architectural river cruise (we took the evening cruise so that we got to watch the city light up as we went – highly recommend that!).

We also hung out in Lincoln Park (both the neighborhood and the actual park) for the better part of a day, and then we walked through Old Town and the Gold Coast on our way back to our hotel. The neighborhoods are one of the things that make Chicago so special, I think.

Here are some of my favorite pics from the trip, with where we stayed and where we ate at the end of the post. I also saved all my IG stories from the trip to a highlight.

University of Chicago
Hyde Park/University of Chicago
Hyde Park/University of Chicago
Tom deciding whether to tempt fate.
Kincade’s in Lincoln Park
Lincoln Park
Lincoln Park
We made a sweet friend in Lincoln Park. Her name is Leia and she has hip dysplasia so she rides in style.
View from Lincoln Park
The Halloween decorations were amazing – Chicago is a BIG Halloween town.
P.O.S.H. Chicago
Architectural River Cruise
Architectural River Cruise
Architectural River Cruise
Ralph Lauren Restaurant

Where we stayed

The Westin Michigan Avenue (Gold Coast). We had Marriott points so we chose this hotel on the very north end of the Magnificent Mile, near the Hancock Building and Water Tower.

Where we ate

Medici on 57th (Hyde Park) We grabbed lunch at this casual place near the University of Chicago.

Monteverde (West Loop) Hip (way more hip than us) Italian restaurant where they make pasta by hand (you can watch from some tables while you eat). The food is delicious; this is a great place for foodies (which we’re also not, but we managed ;)).

Kincade’s Bar & Grill (Lincoln Park) We grabbed lunch and watched the first half of the KU game at this Chicago hangout for KU fans.

Lou Malnati’s Pizza (Gold Coast) We have to get our Chicago deep dish fix while we’re in town.

Wildberry Pancakes and Cafe (Streeterville) Great breakfast and it’s a big place so the wait on a Sunday morning wasn’t too bad.

Rosebud Steakhouse (Magnificent Mile) We gave up our Sunday night dinner reservation at another restaurant to go on the evening river cruise and afterward as we struck out at restaurant after restaurant who were full, we called Rosebud tired and hungry and they said “come on over, we’ll take care of you.” Even though they were packed we snagged an outside table and had an amazing dinner. I still get warm and fuzzy thinking about it.

Ralph Lauren Restaurant (Magnificent Mile) I’ve been wanting to eat at RL for a while and all I can say is WOW. It was great food, beautifully served, and the restaurant itself is stunning. If you get a chance to eat at one of the RL Restaurants (they’re in NYC, Chicago, Milan, and Paris) do it!

P.S. Washington D.C. trip report and four fun things we did in New York.

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  1. Debbie Wilson says:

    Beautiful pictures! Chicago is one of my favorites cities but we haven’t been in a few years either. It looks like a wonderful trip.

    1. Time to book a trip, Debbie!

  2. This makes me want to go visit Chicago again! Love it there! Thank you!

  3. Pat in Chicago says:

    Your pictures are beautiful. I love that you love my city so much. It is a great city. The crime has gotten out of hand and that makes me so sad. Thank you for showing how beautiful this city truly is.

    1. Glad you enjoyed the pics of your beautiful city, Pat!

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