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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.  

The world’s longest continuous bar is on the second floor of the open lobby

The busy bar has a gorgeous view of the city at night, and plenty of screens for your entertainment

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!

Blues Brothers 

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.

Midway Airport

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!

Returning Home

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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