We went to Chicago in March 2022. Below find our guide for a trip to the windy (and very cold) city. We went for a long weekend which was a perfect amount of time to see a few sights. I think that you could easily spend an entire week if you have the time.
Things to Do:
Chicago has a lot of free attractions.
-Chicago Riverwalk- the Chicago riverwalk is on the South side of the loop. It’s a great way to get close to the river and see the buildings from a different perspective.
-Lincoln Park Zoo- The Lincoln park zoo is free and open all year. When we went, most animals were inside. We were still able to see a lot.
-Lincoln Park Conservatory- This small botanical garden is a great stop to get out of the cold. You probably only need about 30-45 minutes there. You do need to book your free tickets online. I did it while we waited outside. We went right at opening on a Thursday though. Weekends might be busier so more advance planning might be needed.
-Millennium Park- This is where the famous cloud gate sculpture is located. We went both during the day and at night. As you might expect, it was far less crowded at night.
-Dyeing the River Green- Every year, the Chicago Plumbers Union dyes the River green on the Saturday before St Patrick’s Day. It starts in the morning around 10. It probably takes about one hour for them to complete the dye. The next day, the green was still fairly vibrant but had started to fade a bit. The tradition can be watched from the sides of the River. There are a lot of rooftop bars that have viewing parties too. We upgraded our hotel room so we could take in the view indoors. We thought that the extra cost was well worth it because it was only 8 degrees on the day.
-Chicago St Patrick’s Day Parade- Although this was another free activity, we found the parade to be very crowded and most were partying rather than watching the parade. We didn’t stay long.
-Architectural Boat Tour- The boat tour was interesting and had great views. I would suggest that you are flexible on the day that you go. I would also suggest that you book the tours that leave from the Riverwalk. We had to walk to the navy pier and they ended up canceling us and rescheduling us to go from the Riverwalk which was across from our hotel. It wasn’t a huge problem but it ended up taking more of our day than we expected.
-Skyline Viewing Decks- There are two viewing decks that I’m aware of in Chicago. One is at the Willis tower and the other is the former John Hancock tower, 875 North Michigan Avenue. The Willis is more popular and a bit more expensive. My husband went to the Willis tower during his first trip to Chicago and felt it was worthwhile. An alternate option to paying to go up the tower at 875 North Michigan Avenue is to go to the Signature room at the 96th Floor. We did this and felt that it was worth it. Try to sit near the windows. The Signature Room is pretty dated but their drinks are reasonable considering the view. They even have their own beer called The Signature Top View Brew from Crystal Lake Brewing.
-Tiffany Dome- located in the Chicago cultural center is a massive Tiffany glass dome.It is a great example of Art Deco Architecture. The cultural center also has a few art exhibits and an exhibit on the great Chicago fire.
-Museums- There are tons of museums in Chicago. We ran out of time and didn’t get to see any of them. Next time!
Restaurants:
-Monteverde- This was our favorite restaurant of the trip. Everything that we ordered was delicious. The menu is constantly changing. It is composed of modern takes on Italian pasta dishes. All pasta is made in house.
-The Berghoff- This restaurant makes you feel like you jumped back in time. It’s an old style German restaurant with house made beer. The restaurant was only a few blocks from our hotel.
-The Dearborn- The Dearborn is a modern Irish pub. My husband, Alex, went when he was traveling for business. He said that we had to go back and I’m glad that we did. They pour perfect Guinness. It was the perfect spot to go to brunch before heading to see the river dyed green.
-Lou Malnattis- You have to try deep dish pizza at least once In Chicago. We ended up at Lou Malnatti for lunch. The pizza and wings were both very good. Keep in mind that you may have to wait a while for your pizza as the deep dish takes longer to cook.
-Al’s #1 Beef- This fast food restaurant has a few locations throughout the city. We had a classic beef sandwich and a Chicago hot dog “dragged through the garden” style. We shared them and it made for a quick and easy lunch. Like the pizza, you have to try the Italian beef and hot dogs while in Chicago.
-The Chicago Athletic Association- This old athletic club was turned into a hotel in 2015. The developers maintained a lot of the building’s old charm and features. There are few areas that are accessible for non hotel guests. There’s the game room which is a bar with pool, shuffle board, etc. The game room was pretty crowded so we went up to the rooftop bar. The bar is enclosed but there’s a terrace to enjoy drinks outside. As I mentioned, it was very cold so they had a fire pit going to keep you warm.
-District Brew Yards- At Distrct Brew Yards, you can serve yourself from 40 taps from 4 or 5 breweries. You get charged by the ounce. In order to start pouring, you tap a card that’s linked to your credit card. We had a lot of fun trying the many options. There’s also a food stand where you can order bbq style foods.
Other places that we enjoyed
-Happy Camper Pizza- Wrigley
-Miller’s Pub
-Bar Mar by Jose Andre
Transportation
We did a lot of walking as we normally do.
The CTA is probably the easiest way to get around. The trains are reliable and arrive every few minutes. Beware that like any city transportation system, the trains aren’t the cleanest. The benefit of the above ground portions of the train system is that you get to see the city while you ride.
Since we had time on our hands, we took the blue line train from the airport to the hotel. It’s the least expensive option to get to the city center from the airport. It’s a little annoying to carry bags but it was worth it to save. Alternatively, you could take an Uber or taxi. Chicago is infamous for its traffic so taking a car from the airport might not save much time and it will certainly cost more. I don’t think that it’s worth renting a car in the city. Given the elaborate transportation system and availability of uber and taxis, it just isn’t necessary.
Travel with Rebecca 