4-DAY Chicago, Illinois ITINERARY

Chicago, on Lake Michigan in Illinois, is among the largest cities in the U.S. Famed for its bold architecture, it has a skyline punctuated by skyscrapers such as the iconic John Hancock Center, 1,451-ft. Willis Tower (formerly the Sears Tower) and the Neo-Gothic Tribune Tower. The city is also renowned for its museums, including the Art Institute of Chicago with its noted impressionist and Post-Impressionist works, per Google.

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Must do, must see, must try:


Commonly known as 'The Bean', this art piece is sure to catch all your good sides with no seams and high reflection.


Goodbye diet, yes to trying a Chicago dog fully loaded, or a deep-dish pizze. Heck try both!


Learn about the architecture from a river cruise, or venture to the 103 floor to see all of Chicago.

The Perfect 4-Day Chicago Itinerary


AirBnB close to the canal, Millennium Mile or near the Art Institute 

Hotel: Hyatt Regency Chicago ($$)


Mid-April was rainy and cold and windy, ideally go between milder weather of late Spring, early summer, and early fall.  


Walk-able layout, but you'll want to Lyft to the outskirts. Don't rent a car, it's too expensive paying for parking and not worth it.


Language is English

Currency: US Dollar


Great city for a sweet weekend away with a love or friends, birthday celebration or long weekend away. A lot of day time activities and night; bars, restaurants and sights to visit.

Chicago is a bustling city that attracts hundreds of thousands of visitors each year. Besides the breath-taking architecture, Chicago offers some great attractions, beautiful museums and elegant city parks.


Chicago was a birthday trip that I visited with my mother, and it was a great location to visit. There is so much to see and do - from learning the history of the Great Fire to the houses of Frank Lloyd Wright, to trying not to be blown away; eating all the pizza and hot dogs, this city is truly amazing.

Day one

Early flight so early arrival; check-in at the hotel and drop off bags

Walk up Michigan Avenue to shop the Magnificent Mile

Have an afternoon snack from Garrett Popcorn Shops ($$, Popcorn), try the combo of Caramel Crisp and Cheese popcorn

Get a picture with the Chicago sign at The Chicago Theatre

6:30 PM Dinner: The VIG Chicago ($$, Gastropub)

8 PM – The Second City; time spent is 3 hours depending on your show, $​30 USD

  • Show: Fantastic Super Great Nation Numero Uno

Day Two

Breakfast: find a coffee cart for something warm and granola

8 AM – Skydeck of Willis Tower (Sears Tower); time spent is 1 hour (not including time spent in line), Basic Admission for $23 USD

  • Opens at 9 AM, but get there beforehand so you can be first in line to catch the elevator up

10 AM – Transit or walk to Millennium Park

10:30 AM - Art Institute of Chicago; time spent 4-5 hours, Fast Pass $30 USD

  • Get your tickets beforehand so you don't have to stand in line - which usually takes 45 minutes

Noon – Lunch at Terzo Piano ($$$, Italian) in the museum - make a reservation, it gets packed​

Across the street is Cindy's ($$, American) rooftop bar, rest your feet and get a cocktail

  • There's another bar and game room around the corner from the check-in desk if the line for the rooftop bar is super long, but you'll miss out on a great view​

Walk up Michigan Avenue to the Chicago Riverwalk

6:00 PM Dinner: deep dish pizza at Lou Malnati’s Pizzeria ($$, Pizza) or Giordano’s ($$, Pizza) 

Dessert: Public House ($$, American Sports Bar)

  • Happy Birthday to me! Cake Shake - mix of ice cream, craft beer, sprinkles, icing & a giant slab of cake

7 PM Show & Drinks:

Day Three

9 AM Breakfast: The Bongo Room ($$, American Brunch), try the French Toast

10 AM – 1 PM – Frank Lloyd Wright Tour; buy tickets in advance

2 PM – Chicago Crime & Mob Tour; time spent is 1.5 hour, $35 USD

5 PM – Go to the top of John Hancock Tower (aka 360 Chicago Observation Deck – best seen at night); time spent is less than 1 hour, $20 USD

  • 360 Observatory has the tilt - a glass incline that leans you out over the city​

6 PM Drinks: Signature Lounge ($$$, Cocktails) on the 96th floor of the Tower

  • MUST experience - enjoy it sipping an esquire martini

  • PRO TIP: If you have a reservation for dinner, you get to skip the waiting line​

7 PM Dinner: venture down one floor to the Signature Room on the 95th floor

Day Four

9 AM Breakfast: Kanela Breakfast Club ($$, Breakfast) 

  • Try: Loukoumades with warm honey for dipping; a monkey bread skillet; Nutella S’more Waffles; Chicago Waffles...basically everything

10 AM – Chicago Architecture River Cruise; tour is 75 minutes, $70 USD

  • Bring sunglasses and sunscreen if you are prone to burning​

  • Day Options: Hop on transit to Wicker Park for shopping Chicago’s trendy stores or Lincoln Park Zoo; time spent is 2 hours, FREE. Or tour Gold Coast neighborhood. Grab a coffee before heading to Rush Street.

1 PM Lunch: Portillo's ($, hot dogs) for "The Best" hot dog - which is what they call it

Back to the hotel to check-out

Goodbye Chicago. Head home

helpful links
Travel a GO-Go

Use the Google map on the left to get a lay of the land and see all the fun spots that you'll visit. Download the free PDF by clicking the icon below to have this itinerary at your finger-tips. 

How to Use the Map: Click the tab in the top left hand corner to view the layers (days, points of interest, route).

If you click the star, this map will be added to your Google Map account. To view, open your Google Maps, click the menu button "Your Places", select the map and it will open. 

Shop my Travel essentials

Chicago is a bustling city that attracts hundreds of thousands of visitors each year. Besides the breath-taking architecture, Chicago offers some great attractions, beautiful museums and elegant city parks.

This was also the chosen spot for a birthday celebration with my mother. We had the most amazing time learning about the history, stuffing our faces and walking through the wind. Seriously looking forward to going back and seeing more. Chicago has so much to offer and then some, just bring a really warm jacket. 

Windy city is an understatement, 

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Typical travel websites will give you the top 10+ attractions to visit, their experience and the perfect photo to prove it. ItineraryTraveler provides everything you want to do, all in one place. Everything from prices, how long to spend at an attraction to options for your day, food recommendations and more.


The other sites may list what's great about a city, but not how to do it all. I like to plan so keeping track of how I spend my day in this city helps when friends ask for recommendations of what to do. Keep in mind, it's your trip so mix-up this itinerary, add some events, remove some, make it your own and enjoy your trip. 

If you want more, a personalized itinerary may be the route to take. Get more information by clicking Your Trip

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