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48 hours in Chicago
Paul and I had the BEST time in Chicago on a weekend trip. I found an excellent price on flights via the app Hitlist, and because we went in the off-season, we got a really excellent deal on one of the best hotels in Chicago, the Hyatt Regency Chicago. I couldn’t resist, so Paul and I booked a trip leaving on Friday morning and returning home on Sunday around noon. Ultimately, I decided to book us on a flight with Southwest for free using points!
I’d actually had an opportunity to visit Chicago before for a conference. I had such a good time that I’d convinced Paul to come with me. Now HE loves it so much that we are really looking forward to spending a week in Chicago exploring around in the future, but for now, here are some excellent things to do if you have 48 hours to spend in Chicago!
I hope these travel tips help you Love Travel/Travel Well!
Hyatt Regency Chicago
I’d like to start by saying that this is the second time I’ve stayed here, and for a reason! Hyatt Regency Chicago is one of my favorite hotels. Lots of bars and restaurants inside, a 24 shop and coffee bar, excellent rooms, clean and modern, and excellent service.
I used the Hyatt app to check in online that morning before we’d even left Jacksonville, and about 10 minutes later I got a message saying our room was ready and sending me my digital key– at about 6:30 in the morning! In addition, I was able to upgrade to a high floor with a city view for a good price. When we got there, because we were already checked in and had a key, we went up to our room on the Board of Trade floor, and were greeted with a clean, comfy room with everything we needed and a great view!
We ate dinner downstairs in one of their many restaurants– a classic Chicago dog with cut up peppers, pickles, onions and relish.
Don’t dismiss a hot dog in Chicago! They’re known for their excellent food (everything is VERY good here) and even their hot dogs can leave you crying. Our buns were like a delicious croissant.
Daley Plaza for Christkindlmarket
We were lucky enough to be there on the opening night of the Christkindlemarket located in Daley Plaza. The market is free and very much worth a visit. It was cold out, but joyful, with many happy Chicagoans gathered together after work, browsing the crafts, eating fresh made traditional German pastries (yum… warm chocolate) and drinking warm spiced wine. The buildings set up in true German fashion and made out of wood, which for some reason impressed me to no end.
Every year they sell a small German boot to order the hot drinks from and collect. Naturally, I had to purchase a little Christmas themed boot as a souvenir. I also went into Hermann the German’s candy shop and enjoyed smelling on the freshly roasted nuts while I browsed through imported European sweets and dreamed of Christmas in Germany.
Photoshoot- Cloud Gate (The Bean), Art Institute, Chicago Cultural Center
Ever since we started the travel blog, Paul and I have been getting photoshoots. It’s hard to get great photos of yourself, and so handy to have a professional photographer! We book our photoshoot from AirBnB Experiences, and couldn’t have been more pleased.
One huge plus to hiring a photographer is that they know the best places to get the best views of the highlights of the town. In this case, we were able to see Cloudgate (“The Bean”) in Millenium Park, have a narrated walk about the history and culture of Chicago, see beautiful views of the city, stop at a hidden gem for photographs in the Art Institute, and explored the Chicago Cultural Center (our original meeting place), where we explored around and saw some gorgeous architecture in Chicago’s first public library, including a beautiful view of the world’s largest Tiffany stained-glass dome.
Lunch at Giordano’s
After our photoshoot, we decided to check out the famous Giordano’s for class Chicago deep-dish pizza. The food was excellent and we got to squeeze in another classic Chicago food icon on our short trip!
Paul and I have the same favorite movie: The Blues Brothers! We decided to hire an Uber for the afternoon to take us out to 4649 S Prairie Avenue, the location of the fictional Ray’s Music Exchange! Unfortunately, the pawnshop, Shelley’s, that occupied the spot in real life is now closed, but fortunately, the mural in front of which they had the massive street dance scene is still there.
The mural is faded, which was sad considering the neighborhood had many, many colorful new murals nearby. Perhaps someone will come along and restore the mural, which not only recalls the movie, but is an homage to Chicago blues. I’m so glad I got to see this with Paul before it fades away entirely.
The Signature Room at the 95th (John Hancock Tower)
We took the Uber over to The Signature Room at the 95th, which is on the 95th floor of the John Hancock Tower. Most people who visit Chicago pay about $30 a person to visit observation decks like the ones at the top of the Willis Tower. Here, for the price of a couple of drinks, Paul and I were able to get almost 360-degree views of Chicago from high up.
P.S. The women’s bathroom has the best view from the entire restaurant, so if you can go in there, take advantage of the opportunity!
The mall across from the John Hancock Tower (Water Tower Place)
After our drinks upstairs, we walked across the street to Water Tower Place, an indoor, 9 story mall, movie theatre, and condominium combo. We aren’t big shoppers, though they offered a nice selection. We went inside, however, to find a Walter Peyton bobblehead for our friend, and we were successful.
House of Blues
Did I mention that we love the Blues Brothers? Whether you’re a fan of the movie, Chicago blues, blues in general, live music, good food, or a great atmosphere, you’ll find the House of Blues has all of those things! We hung out and after a full day walking around the city, finally went to the hotel and crashed.
Perhaps this seems silly, but we had a GREAT time in the airport! Don’t forget to make use of your time in any airport as there usually is some kind of cool local cultural attraction. In this case, we toured a WWII exhibit, looked for Nuts on Clark, and ate at a delicious Irish pub for lunch!
Well, as usual, we wished we could stay longer on our trip. However, we packed a LOT of fun into just 48 hours in an incredible city. We can’t wait to return!
I hope this list helps you plan a fun 48 hours (or more!) in Chicago!
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I am impressed, you packed in alot in 48 hours in Chicago. There is a lot to see and do there
Wow for a short trip, it was jam
Packed with fun things to do. I’ll keep the photographer aspect in mind for my next trip!
The candy looks amazing first off. I have to go to the Windy City. Thanks for sharing.
Wow this looks like a great trip. I did Chicago for a weekend as well while there for a conference so I got the hot dog, pizza, and the aquarium and just some walking nearby the hotel. Looks like I need to return.
What a fun weekend! I love Chicago and am lucky it’s only a few hours away!
I think it’s amazing there is a Christkindlmarkt in Chicago.
I’ve stayed at the Hyatt Regency in Chicago a couple of times. Great views and location! Love this itinerary. I need a Chicago fix soon!
What a perfect weekend to go! I love a good Christmas Market 🙂 I have never been to Chicago but if I go, I’ll be checking back here for the recommendations!
You had me at hot dog (that is the best looking dog I have ever seen). Also, you did ALOT in 48 hours. I bet you had to get home for a rest, LOL.
Chicago is so awesome. Hard to pack everything in 48 hours but so worth the effort!
I love Chicago. Looks like such a fun time!
It’s been a while since I’ve been to Chicago. I need to go back. That hot dog looks really amazing. I haven’t had a hot dog in Chicago. The next time I go, I’ll have to try one of those!
I’ve never been to Chicago, but I would love to see it – especially in the summer! I’m not a cold weather girl. Great Ideas for some fun!
Sounds like my kind of weekend! I want to go to that german market! I hope to get to one in actual Germany soon but Chicago is closer. Lol.
What a great 2 day in Chi! We used to live there and this brought back memories. Now I want a Chi Dog, yum!
There is a lot to do in Chicago!
A very long time ago my husband and I visited Chicago for an award ceremony for his job. Clearly we need to go back and enjoy more of the city. Thanks for writing this article!
I must be hungry because those french fries and truffles looked amazing! Next time I am there I will be visiting the truffle location.