How to See Chicago in a Weekend

Our “thing” lately has been road tripping to cities that we’ve never visited before, and exploring the sh*t out of them over a long weekend. Long weekend adventures give us the chance to cut back on vacation days while still taking time off to see more places and experience more things. While this isn’t always the best way to explore somewhere new, it is definitely do-able and enjoyable. Our most recent weekend getaway was in Chicago, and if you want to see Chicago in a weekend, here is what we did and how we did it in so little time!

First thing’s first: research, research, research!
Talk to your friends & family, search trip advisor, use Google (or other search engines) to figure out what you want to see and do in a weekend. A co-worker of Alicia’s had suggested looking into the Go Chicago Card and it proved to be worth it. With the purchase of the Go Card, you have access to over 25 attractions, as well as line-skipping privileges in a lot of situations. We were able to skip the line at Willis Tower, Art Institute of Chicago, 360 Chicago and more. We also received discounts on food, along with other perks! Time-saver, for sure!

Make minimal formal set-in-stone plans.
Go with the flow! We had made a mental list of all of the attractions that we would love to see while we visited, but we knew that there’d be no way to see each one over the span of a weekend. We knew for sure though that taking a tour (or 3) would ultimately be a great way for us to see a lot of the city. With our GO Chicago card, there were many tours that you could select from. The afternoon that we arrived, we took a river tour, and for our “full day” of adventuring, we took the Big Bus Tour (which had the option to jump off and on at multiple locations around the city throughout the day) and also a lake tour. All three were fantastic, and worth the time. They had great photo opportunities and we saw and learned a lot about the city. It was a great way to see a lot of Chicago in a weekend.

Avoid museums if you can!
Having spoken with our first tour guide when we were starting our day with the Big Bus Tour, we had asked for suggestions of what the best way to fit in as much as possible during our weekend in Chicago. She had recommended that we not try to do the museums because of the fact that they’re enormous and literally take hours to go through. We politely nodded and told her that tooootally made sense, knowing that we were still going to try to see at least one anyway. When we hopped off the bus at Millennium park only to find out the the Art Institute of Chicago was very close by, we knew we had to check it out for ourselves and “only stay for an hour”. By the time we got in (thank God for our Go card – we jumped the line in front of at least 100 or so people waiting), we tried to quickly walk through to see everything. This was useless. There were WAY too many cool things that we stopped to look at. Thinking we had seen everything that we wanted to see, we realized that already an hour and a half had gone by. Oops!! We decided to head out of there, only to realize that once we were back on the bus, we had missed an ENTIRE section! Dang! So, long story short – the tour guide was right. You are going to take a large chunk of your day going through only one museum. If you’re only in Chicago for a weekend, and especially if this is your first visit, be conscious of how you spend your time. Save the museums for your second visit if you have a huge list of must-sees before you leave… unless of course your sole purpose of visiting Chicago was to see one museum. Then in that case, go nuts!

Make Reservations.
Okay, so, we did previously say “go with the flow”, but if ever you are able, try to book reservations for restaurants that you want to visit ahead of time. With that being said, there are many restaurants in the downtown area that don’t accept reservations because they are constantly busy. Those restaurants typically do have a wait list that you can add your name to, but then there’s waiting of an hour or more before you’re seated, and then more time to wait until you’re actually given your food. To avoid these wait times, try to plan in advance. Put your name on a wait list earlier in the day (say, an hour or two before you plan to eat) and then go do an activity nearby such as taking a stroll down the Magnificent Mile for some shopping. By the time you’re done, you’ll have worked up an appetite and will be seated at your restaurant of choice within minutes of arrival! By doing this, you can make the most of your time, instead of waiting around for a table.

Central Locations are Key
Last, but definitely not least, if you’re visiting Chicago in a weekend, try your best to book your stay at a centrally located hotel. You’ll be in walking distance of so many more attractions, and can easily catch public transit or an Uber/taxi to where ever your little heart desires. We stayed at the Wyndham Grand Chicago Riverfront hotel and it was an easy walk to many places, including the river cruises, the river walk, the magnificent mile, lots of restaurants, and so much more. Michigan Avenue was one block over from us, and many attractions and tours took off from that street – a great starting point for a lot of adventures!

Our visit to see Chicago in a weekend was definitely a success, especially with the tips we received from friends and people that we met along the way. Do you have any other tips that we could add to this list? Feel free to leave them in the comments below!!

Happy traveling!

–The Calkins’

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