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Weekend in Chicago

I get asked a lot, what is there to do in Chicago? So instead of providing a boring answer, I decided to create a comprehensive free Weekend in Chicago guide. I live in Chicago and there is plenty to do that isn’t your typical touristy things.

This weekend travel guide is for tourists traveling for around a 3-5 days in Chicago. This guide is meant to give essential information, obvious sights, how to travel like a local and how I would spend a weekend in Chicago. This guide is designed to maximize time and money spent for people who are spending only a short time traveling here.

 

The Essentials

The basics you need to know

Like a Local

Chicago from a more local point of view

My Weekend Itinerary

How I would spend my weekend

The Obvious Sights

The tourist sights everybody knows

The Essentials

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Getting In
Costs
Getting Around
Best Weekends to Visit
Safety

Like a Local

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In this section I’m going to list how to travel in Chicago like a local. You’ve probably guessed that Chicago has so much more to offer than the typical sites you already know.

Eating
Doing
Seeing
Going out
Getting Out/Daytrips
Etiquette and Other Advice

My Weekend in Chicago Itinerary

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In this section I’m going to list out the perfect Chicago weekend for me. This is meant to help inspire a realistic goal for your weekend here and I’m here to help make sure you do the most important things. Typically a weekend is from 3-4 days but people may have an extended weekend for up to 5 days, so I’ll keep in mind a range from 3-5 days.

This is a curated guide and not meant to be followed strictly. This is just merely a suggestion of the things I would see in Chicago in retrospect. If you’re in town for holidays like Christmas or St. Patrick’s Day then trade out some of these other events to go to things like Christkindlmarkt or to see the St. Patrick’s Day Parade.

Day 1:
Day 2:
Day 3:

The Obvious Sights

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Chicago has many iconic sites which is why I wanted to shortly listed them. Some of these essential but since most people know what these are I’m not going to spend too much on them.

Cloudgate
Willis Tower (Formerly Sears)
Art Institute
Field Museum
Navy Pier
Shedd Aquarium
Adler Planetarium
Millennium Park
Grant Park
Architecture Tours
Michigan Ave (Magnificent Mile)