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Chicago three-day itinerary

Updated November 21, 2021 by Thiago Khoury

I finally published a script in Chicago to make life easier for those who read the tips on the blog and imagine a way to gather them in a trip of a few days.

Yes I know the post title is Chicago three-day itineraryand that’s what I did using colored pegs on this interactive map that you can open on your phone – but know that it’s going to be a blast and if you spend a lot of time at any of these attractions three days probably won’t be enough.

Well, the other tips I give throughout the post, but remember to use this itinerary to your advantage: modify it so that it fits in the best way with your travel time!

Chicago three-day itinerary

Day 1: Magnificent Mile and surroundings

I used two blue pegs to mark what I consider the touristy ends of the Magnificent Mile: the observatory atop the John Hancock Center and the ticket office for the Chicago River boat tour. There are two attractions that have already been painted here and I loved meeting them, I recommend them to everyone.

Read on for the basics of Chicago:

+ Chicago: first impressions

+ Where to stay in Chicago (two tested hotel tips)

+ What travel insurance to buy for the United States? (with discount coupon!)

+ Tips on where to eat in Chicago

+ Shopping in Chicago

Just don’t forget: Magnificent Mile is the avenue marked by the two blue pins that appear on the map, but the Magnificent Mile region encompasses the first few blocks that cut it on both sides – looking at the map, River North on the left and Streeterville on the right side.

Remembering that I already explained the geography of downtown Chicago well, I even did a neighborhood by neighborhood.

Be sure to walk through everything. Well, more or less: Streeterville has few attractions, I remember that in addition to some spaced restaurants, it has one of my tips for lodging in Chicago and a delicious place to have breakfast, in the most it’s the navy pier which I found extremely family, I don’t believe it entertains friends traveling without children.

A tip to get to know the left side of the Magnificent Mile, the neighborhood they call River North, is to go through the red and purple pegs, which are my tips on where to eat in Chicago. That way you go through the busiest streets: Ohio, Ontario, Erie, Huron and Superior, in addition to Oak at the end and State that is perpendicular to them all.

Day 2: The Loop and Museum Campus

The Loop is a continuation of River North, two regions separated by the Chicago River. Basically the difference between them is that The Loop is much denser, fuller and busier. The type of purchase also changes, there are many department stores and fast fashion brands.

I used yellow pegs to show you the main attractions in the area, but how you get through them depends on where you start your day (actually, where you’ll be staying): Millennium Park, Art Institute of Chicago and Willis Tower/Sears Tower .

The famous Chicago Theater on State Street

Millennium Park is the one with the huge silver bean. It is beautiful and without a doubt worth knowing and walking around. If you like art galleries, it’s worth going down to the Art Institute of Chicago, especially if you can combine the tour with lunch and try the delicious restaurant there.

Whether or not it’s worth walking to the Willis Tower is up to you: read what I think about it to decide whether it’s worth choosing between the Hancock Center observatory or her observatory – or climbing both if that’s the kind of program you like.

The other yellow pins are from Buckingham Fountain and the Field Museum. The fountain is beautiful and is part of the lakeside path that leads to the Museum Campus, where not only the Field Museum is located, but also the aquarium and planetarium.

Well, we can sum it up like this: you have to go through (1) Millinnium Park and you have to meet the little brains of The Loop that is famous for having State Street and the blocks that cut it, but if you’re going to get to (2) Willis Tower and whether you go down to (3) the museum district depends on the type of program you like: getting to know everything and going wild in Chicago or spending the day around State Street?

Day 3: Lincoln Park and surroundings

I used green pins to show three places that I loved visiting in an area that is not part of downtown Chicago, but nothing too far, on the contrary, it is very close: Lincoln Park is huge, but right at the beginning there is the Chicago History Museum which is amazing.

Those who enjoy home shopping are worth following Chicago’s North Avenue, the one that starts at the museum, a kilometer before the home decor, kitchen, table and bath stores start popping up on both sidewalks.

In this post I tell you exactly what I did walking through Lincoln Park, I even gave tips on where to eat in those parts of there.

Me my mom at Apple on North Avenue

What else to do in Chicago?

Well, now it’s up to you: if you have a fourth day in the city, you can just do everything I say above calmly and repeat what you liked best on the last day, or you can add an outlet day that is at, maximum, an hour’s drive from the city centre.

+ Discover the two outlets in Chicago: Chicago Premium Outlets and Fashion Outlets of Chicago

Or you can visit Lakeview, which is a very charming residential area and also has options for where to eat and things to see, but all I know there is the Blue Man Group.

Then give your tips on what to do in Chicago and say if this script worked!

Other blog tips for planning your trip:

Already know where to stay in Chicago? I made a list of the best options around the Chicago Loop, but I prefer the Magnificent Mile area, in fact, I recommend DoubleTree and Whitehall with my eyes closed!

Have you already purchased travel insurance? Insurance is essential in the United States, especially in times of covid! The Insurance Promo comparator offers at least 10% off for blog readers and even pay on the card!

Can you travel without a cell phone? Do not forget to leave Brazil with your American SIM card with real unlimited internet – and through the blog link you will take at least 15% off and free and unlimited calls to Brazil!

For rent a car in the usa for the lowest price search all rental companies at once on Rentcars. They have an office in Brazil with service in Portuguese!

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