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Trip report- We love you Chicago!

Thought I would post a quick re-cap of our 4 night trip to Chicago since if you are like me, you are dying for some trip reports on this forum! Sorry it's not Europe, yet!
The impetus for this trip was Alaska Airlines new direct flight from Anchorage to Chicago and I had never been to Chicago. My husband was there once on a business trip. He raved about the architecture and that was enough to make me want to go. Also, we love food and eating was a primary focus of the trip.
We flew AS airlines direct on an evening flight and got to Chicago in the am. We did not get much sleep, so we did drag a bit that first day, but soldiered on with our plans. After getting settled in to our hotel Londonhouse (great location, downtown by the river), we took an Uber to Au Cheval as my research suggested the best burgers in the city there. They did not take reservations, so unfortunately, we got there and it was a 2 hour wait! For lunch! Ok, a bit shocking and we moved on and had burgers elsewhere.
Then it was time to meet up with my bestie and her husband who were in Michigan City visiting family at the same time we were to be in Chicago, so they took the train into the city to meet up with us. I had not seen her in 2 1/2 years. We took the Architecture boat tour on the river with them (something they had never done, surprisingly) and just had a great time, fascinating to hear about the buildings and history of Chicago. I picked out my favorite. The Regis building (almost done). Then we went to dinner at Monteverde, which was excellent.

Day 2- We visited Millenium Park and the bean, and the Art Institute of Chicago, where we finally found the Thorne room (geez, on the bottom floor, it was hard to find). I thank forum member Carol for this as I am not sure if we would have made the point to look for it if she had not mentioned it to me. It was fantastic and amazing. Then we saw the Impressionists and the American Gothic picture and works by Georgia O'Keefe. What a great museum and after 2 1/2 hours we needed to be away from the many, many people there, so we left and had lunch along the Michigan mile and visited the Chicago Architecture Museum which was right next to our hotel. Back to our hotel to freshen up for dinner. A special meal at Smyth & The Loyalist a two star Michelin restaurant, which we throughly enjoyed.
Day 3-We did the Architecture Museum & Big Bus tour of the neighborhoods of Chicago, a 90 minute tour which got us away from the downtown area and we got to see how people live around the city. Then we took the public bus out to the Lincoln Park area to see the Chicago History Museum, which gave us lots of information about you guessed it, the history of Chicago. We walked along the Lake Shore back to the hotel and it was interesting to see people hanging out at the beach with the Chicago skyline right there! I guess not having traveled lately to the big city, I just kept marveling at the skyline. We have no big buildings in Anchorage that are anything like Chicago. We grabbed a quick bite and had a rest back at the hotel and later walked to our steak dinner at Hugo's Frog Bar, as my husband insisted on a steak house as one of our dinners. That evening, we went up to our hotel's rooftop bar for fantastic nightime views of the city. This was the only night of our four nights it was open, as we had a LOT of rain during our 4 days in Chicago.
Day 4-We had reservations for the Immersive Van Gogh exhibit (thanks forum folks) and took the bus out to Lincoln Park again. We throughly enjoyed this show of Vincent's work. We sat through the whole thing two times. Then it was time for some deep dish pizza at Pequod's Pizza (a bit out of the area so we took Uber). We are not normally deep dish pizza people, but when in Rome as they say! Then we walked around Astor street and the lovely neighborhood near Lincoln Park.

Posted by
3363 posts

Back to the hotel we had a meet up with an RS forum friend who was also visiting Chicago at the same time as us. Hi Chani! We spent a lovely few hours getting to know Chani over some drinks and food at the Purple Pig. A great ending to our four days in Chicago, we flew out the next morning back to Alaska. I loved our visit getting to know Chicago. I like seeing things besides trees and mountains, which is what we have here in Alaska. Now, I think I can say that I have visited most, if not all, of the big cities of the US.

Posted by
23471 posts

A nice report. As a former long time resident of the area, I will have some suggestion for the next trip. You have barely scratched the surface.

Posted by
9875 posts

Tammy, this sounds wonderful ! And you even had the Europe effect of an overnight flight and bleary first day 😜😜

It sounds like you really had a great time -- i am sure it was so special to see your best friend, and then to get to meet Chani.

Thanks so much for sharing your enthusiastic report with us.

Posted by
11368 posts

You did a great job sampling Chicago in four days! We loved living downtown in the Gold Coast( near Astor) and easily walking over to the lakefront and it’s beaches. It is such a fabulous city. So glad you enjoyed it!

Posted by
3961 posts

I enjoyed your report very much! It’s been a number of years since I visited. Fun to reminisce through your experience. How fun to meet up with Chani!

Posted by
6670 posts

I love Chicago though I've had only a few visits. Cloudgate (aka The Bean) is one of my favorite pieces of public art. So glad Alaska Air has a nonstop from Anchorage (makes SeaTac a bit less crowded I guess). I haven't been there in winter, and don't want to after seeing the heaters at the El stations in the Loop. As an Alaskan this may not faze you though.

For your next visit, I suggest the Field Museum of Natural History and the Frank Lloyd Wright houses at Hyde Park and Oak Park. There's also an architecture walking tour (maybe more than one) which shows you buildings you don't see on the boat tour. Thanks for a great trip report!

Posted by
2017 posts

My hometown! Chicago is beautiful in the summer. The lakefront is pretty than NYC and we even have beaches. Glad you had a good time.

Posted by
994 posts

Thanks for the report! It sounds like a great time. Chicago is a nice weekend trip from here, so I go for the weekend every few years. There is always something new to do there!

Posted by
15684 posts

And I had a great time with Tammy and her husband. Hi Tammy!

Now I'm piggy-backing on Tammy's excellent trip report to solicit suggestions for myself for next week. I have been gifted 3 nights at a hotel just south (technically) of the Loop (as Tammy was technically a block or so NE of the Loop). One day will be spent at the Art Institute, as I do on every visit to my home town.

Posted by
1450 posts

Chani.... train out to oak park for frank Lloyd Wright and Hemingway....

Posted by
7050 posts

What's the live music scene like right now? Anything open, even outdoors? That's one of the best things about Chicago, bar none. Also, I love the University of Chicago campus which includes the amazing Oriental Institute Museum and Robie House.

Posted by
4304 posts

Love Chicago. The architectural tour is outstanding. We also rented bikes for a day and rode north past the Zoo. One of the best meals I've ever had anywhere was at Joe's

Posted by
119 posts

I love the Chicago Architecture boat tour and consider it a must-do when visiting the city. I've done it three times over the years, including one New Year's Eve for the nighttime fireworks over the city. If anyone reading this will be in Chicago October 16-17th this year, here's another must-do: Chicago Open House (