Chicago! Walking around downtown Chicago is so much fun as there is so much to see. We spent 24 hours in the Windy City visiting Steve’s crew and had a great time just wandering around and enjoying the busy city life. Being a small town girl, I found Chicago to be exciting!!
We arrived in Chicago on a Saturday afternoon. The traffic was not much fun, but better than we thought it would be. Seeing the skyline on the drive in is a rush!
The Hotel Felix
We reserved a room at The Hotel Felix. We found this hotel to be beyond our expectations. The pictures on the website do not do it justice. The room was comfy and staff were attentive. The lobby was fun and inviting. We even had a great city view from our room. The best part is we were within walking distance of everywhere we wanted to go!
Diary of a Gen-X recommendations for hotels and restaurants are based on our own experiences. We do not receive compensation for recommending at any of these nor are we affiliates of any hotels or restaurants. The only hotels we recommend are places we stayed which were clean, comfortable, and provided exceptional hospitality. The restaurants we recommend are also places we have been to and enjoyed.
Downtown Chicago Neighborhoods
After checking in and dropping off our bags we walked to Steve son’s apartment passing by lovely tree-lined townhomes with lots of character. I had no idea there were such cute neighborhoods in this area.
After checking out their new place, we followed them to the Lakefront Trail and enjoyed walking along the Lake Michigan Shore. So beautiful! Perfect place for a hot day!
After enjoying the Lakefront Trail we headed back to Hotel Felix to get ready for dinner. We were dining with his family and friends.
Topo Gigio Italian Ristorante
Dinner was in old town of downtown Chicago, at the award winning Topo Gigio, a fine dining Italian Restaurant Ristorante. Topo Gigio did not disappoint! The food and service were beyond amazing. I had Spaghetti and Meatballs and Steve enjoyed Shrimp Linguini. The group also enjoyed a delicious Malbec. I cannot remember the last time I had such wonderful Italian food. You can check out this link for more information. https://www.topogigiochicago.com
Jeni’s Ice Cream
After dinner we went for ice cream at Jeni’s. There was no way I could even think of ordering! I was full!! Steve had a peanut butter ice cream and of course I had a bite. It was amazing!!
Downtown Chicago Night Lights
We headed back and enjoyed walking around the city at night. It was a perfect summer night, warm with just a bit of a breeze. It was a nice ending to a fun day.
In the morning we woke up early and headed to the Chicago Bean at Millennial Park. We were hoping to get there before the crowds arrived. There were some people there, but not crazy crowded.
We enjoyed walking around downtown Chicago when it wasn’t very busy. I love the way the old historic buildings and new modern buildings blended together to form the downtown vibe.
This ended our 24 hours in Downtown Chicago. We said our goodbyes and hopped in the car back to Iowa. A quick but fun trip! It is always great being with family!
You will want to wear comfortable shoes and clothes! Also, a good backpack works well instead of a purse to carry your stuff. Keeps your hands free and it’s easier on your shoulders. I like the Hobo River Backpack, it’s stylish, has pockets, is easy to access and comfortable to carry.
34 thoughts on “Downtown Chicago, So Much to See.”
Looks like you had a lot of fun. I haven’t been to Chicago since 2001 (except the airport), and I never made it to the downtown area, just the Magnificent Mile. Would like to see the bean one day.
We did enjoy it! With his son living there now I am sure we will be there more often! I think the Bean is amazing to see and walk under!
Chicago is an endless fun! Come for one day – I have a plan, come for two – I will show you the best of the city, come for a week, for two weeks or more – you can be at some new place every day, and still have a lot to see I guarantee 🙂
Great photos and description of your trip. Love the photos – great angles, landmarks, and other shots giving us a flavor of how to spend a day in Chicago.
We pretty much just roamed but it was so much fun! Goes to prove you don’t have to spend a lot to have a great time in Chicago!
We really just roamed around but had a blast! Goes to prove that you can have a great time without spending a lot of money in Chicago!
The architecture is amazing…such detail. 😊
I love Chicago but have only ever visited in winter or fall so have enjoyed visiting the museums and art galleries.
I have not been there in the winter, but I bet it is cold!
Wonderful pictures, dear. What an architecture ! And your report, your description is awesome. Now, i want to visit Chicago !
Thank you! I can’t take credit for all of the pictures, Steve did his share of picture taking as well. I want to go back for more of the Italian Food!!
Oh, and for some wine, like the one i see, the “Santa Julia”. The funny thing is that i have relatives in Chicago, but still haven’t visit them. The next funny thing is that the wonderful Chicago that we see now in your pictures, becomes a refrigerator during the winter… lol
Yes, the wine was wonderful. Not as wonderful as the Venetsanos wine we had at Santorini, but still wonderful!! Hope you get to Chicago!
Have you ever tried Vinsanto, since you ‘ve been to Santorini many times. It is red and sweet. I like it a lot, dear. I Like it with an ice cube in it… lol
No. I have not tried the sweet but I will try it on this next trip! Isn’t it made from grapes only grown in Santorini! We’ve been to Santorini once so far and are returning this Sept. last year we got back to the states we ordered a case through a distributer in New York of the dry red from Venetsanos Winery in Santorini!
Yes, exactly. It is only made there. There is a whole procedure for this type of wine. There a lot of nice places for relaxing and tasting their wines. One is the Santo Wines, which is high and the view is great. Another one is Sigalas. And i think you would like to visit the Koutsogiannopoulos Wine Museum. You need to have time, on the other hand, there are too many. The small village of Akrotiri is wonderful since it is the prehistorical town discovered of there. A nice place to eat some wonderful fish is Ammoudi (i used to visit the first tavern). And, of course, a tour around the island with a boat ( i don’t know if “King Thira” is still on this tour) watching the sunset is wonderful too.
Wonderful tips!! Thank you! We are definitely going to Ammoudi this time and will look for the first tavern. We have friends going with us and One of them desperately wants to find the best wineries so I will remember these!!! We did a sunset tour Boat last year but our friends are going to do one this year. Thank you again for all the tips I am just so excited I can barely wait!!!
You’ re welcome, dear. Take care and enjoy. If you want anything, some extra info or whatever, do not hesitate to come in touch.
Great post 🙂
Wow! Looks like a great visit to the “Windy City” of Chicago ~ love the architecture!
It was a great time!
What great photos!!! I love some of the angles you used! I was in Chicago 3 years ago on business. My coworker and I snuck out of our meeting early and took the river tour of Chicago. Next time you are there, do try to take that river tour – it is FANTASTIC!!! I had no idea Chicago was so interesting and beautiful! Your photos just added to my reasons for going back there sometime as a fun-trip, not a business-trip.
Glad you liked the photos! I have heard the river tour is great. It is on our list to do one of the times we are there! Thanks for the info!
Wow, Chicago looks fun! And I love the plate with Spaghetti and meatballs, lol 😂
Chicago is such a great city! The waterfront is so lovely to stroll along. Did you try the deep dish pizza?
We did not try Pizza in Chicago yet! We will definitely try it next time we are there!!
Love your combo of city and outdoorsy posts! Keep it up! All good reads.
Chicago is an easy weekend getaway from Toronto. I can’t believe it took us so long to visit. We went in late October and missed the chance to enjoy the waterfront. We did love the chance to see the “Bean” and catch a reflection or two. But as a Civil Engineer, I did enjoy geeking out over all the great building architecture in Chicago. Glad you had a great day in Chicago. We know we have to go back.
Sounds like you had a good time in Chicago as well! It is definitely a busy city!! The buildings are pretty cool!