Exploring Chicago in Two Days: 48 hours in the Windy City
Exploring Chicago in Two Days: 48 hours in the Windy City
Chicago is an amazing city with a vibrant atmosphere, rich history, and diverse culture. We visited while attending Lollapalooza, which gave us some time to explore the city outside of the festival. If you are short on time, here is a guide for some of the best things to do and practical advice while visiting the wonderful Windy City.
This isn’t written as day itineraries, but suggested things to do with the approximate times and cost, allowing you to pick and choose what interests you.
Table of Contents
Chicago Must Do’s
River Architecture Tour
This was a highlight of Chicago for us. It was pricy at $110 per ticket, but so worth it. We had a fantastic volunteer guide who was incredibly knowledgeable, and it was lovely to cruise along in the sun listening to her. The tour is approximately 90 minutes, two hours total including lining up.
Tip: you sit outside so be prepared for the weather. Don’t forget your hat like me!
River Walk
Stroll along this beautiful river pathway from the city right out to Lake Michigan. The scenery is stunning and there are lots of places you can stop along the way for a drink, ice cream, or some retail therapy.
How much time you spend doing this is up to you – you could spend 10 minutes, or hours!
Navy Pier
Situated on the shoreline of Lake Michigan, Navy Pier is a stunning place to visit in Chicago. We thought it would be great to go for a morning stroll and coffee – the morning stroll idea was excellent, but we struggled to find coffee! If you wanted a frozen margarita though, you were in luck.
We didn’t have time on this trip with the festival, but it would be great to come back here in the evening for some drinks, watch a fireworks display, and ride the Centennial Wheel. There are lots of events that happen at Navy Pier, for a list see this website.
Navy Pier is free, but there are lots of attractions you can spend your money on there too. Depending on what you want to do will influence the time you spend here. If you are looking to just walk around it, allow at least 30 minutes.
Wrigleyville and Wrigley Stadium
If you are in Chicago during baseball season, get yourself along to a game. Wrigleyville has an awesome atmosphere, and the game was so much fun (even though we didn’t fully understand the rules). Tickets were reasonably priced, we paid $45 each, plus taxes.
Allow 3 hours for the game and another hour to get in and out of Wrigleyville. For more information, see our guide.
Grant Park
We spent a lot of time in Grant Park, but this was to attended Lollapalooza. If the festival isn’t on, we would definitely recommend adding this to your itinerary. Stroll around the beautiful park and see some of the main attractions such as the Buckingham Fountain and The Bean.
Again, time spent here is up to you, but it is a large park so we would suggest an hour at a minimum.
Deep Dish Pizza
If you visit Chicago you have to try deep dish, right? This could be unpopular opinion, but we tried it and didn’t like it. But you have to try it to know! Lou Malnati’s was recommended to us – be prepared to wait for a table.
Allow a couple of hours for this as you may have to wait for your table, wait for your order, and then eat. A table next to us were stressing because of the long wait and having something to go to afterwards.
Shopping
The shopping in Chicago was great! State Street had lots of options as well as the famous Magnificent Mile. There are also several outlets located within close proximity to the city centre, including Chicago Premium Outlets, Fashion Outlets of Chicago, and a little further away, Pleasant Prairie Premium Outlets.
We went to Pleasant Prairie, which was quite good, there were some good deals but not crazy good. In our opinion, it wouldn’t be worth going unless you are passing.
Time spent shopping is definitely personal preference – some of us could quite happily spend the full two days shopping, and others may not have want this in their itinerary at all.
Practical Info and Tips
Where to stay?
The Loop is the go-to area to stay if it’s your first time in Chicago. There are a bunch of attractions close to it and a lot of accommodation options. Another area that we really liked was River North and we spent a bit of time there too, especially close to Michigan Ave.
How to get around?
Chicago is a very walkable city, so if you like walking and the weather is nice, we would definitely recommend this as the way to go. If you stay within the suggested areas above, you’ll be nice and close to the main attractions. We also used public transport there to get to Wrigleyville and found this easy. Check out the CTA website to find out more about public transport options.
Grocery stores/supermarkets
If you are from North America, you’ll probably wonder why I get excited about this, but trust me, the supermarkets in the USA are so much fun. The aisles are filled with lots of different products to what we have in our small country. We love Trader Joe’s and Wholefoods. There is also a Target in The Loop close to a lot of accommodation options.
Is it safe?
A lot of people were concerned when we said we were travelling to Chicago – “isn’t it dangerous?”. Well, yes as with a lot of big cities, but we felt totally safe in the popular tourist areas and at Lollapalooza. As always, when you travel, be aware of your surroundings and in Chicago stick to the main tourist areas.
Thanks for reading, we hope you found this helpful and enjoy your time in Chicago!
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