How to Spend 5 Days in Chicagochicago is jam-packed with delicious food, places to go out, museums, parks, and more! it is a destination for many and all! explore downtown, the smaller neighborhoods, and of course, the lake front on a trip here...Authorskatherinebeard
DestinationsChicagoItinerary

Day 1

Fairgrounds Craft Coffee and Tea
Grab a specialty brewed cup of coffee at this spot right on Michigan ave.
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Flamingo - Alexander Calder
Stop by the famous, red flamingo to snap a few photos amidst the cityscape.
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Chicago Riverwalk
Walk around the riverwalk for views of the towering overhead buildings, a vibrant social scene with lots of bars and restaurants, and of course, views of the river!
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Chicago Architecture River Cruise
Definitely try to take an architecture cruise too! It's a Chicago classic.
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Portillo's & Barnelli's Chicago
This is a MUST visit when in Chicago. A classic Chicago dog and a delicious slice of chocolate cake are necessary.
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Navy Pier
An iconic Chicago spot, take a ride on the Centennial Wheel for amazing views over the lake. There are tons of restaurants here to grab a bite or a drink if you need a break.
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Giordano's
This Chicago deep dish spot is a must-try and of course, they have a super convenient location at the Navy Pier.
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Day 2

Firecakes Donuts
They even have donut flavors inspired by the TV show: "The Bear."
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Millennium Park
After stopping for delicious treats head to Millennium Park to see some of the most iconic Chicago sights such as the Cloud Gate (the bean), the Crown Fountain, and the art institute.
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Crown Fountain
In the summer, this is a popular spot to splash in cooling waters. In the winter you can still come to see the different faces of Chicago citizens on the fountain towers.
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Cloud Gate
No trip to Chicago is complete without a visit to this iconic art installation. Snap a distorted selfie in its reflection! To enjoy the bean in solitude, you'll have to get up nice and early.
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Lurie Garden
Wander around these gardens, admiring the local and native species, as well as the hedges inspired by the saying, the "city of tall shoulders." it is truly an oasis from the rush of Michigan ave and the touristy Millennium Park.
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Nichols Bridgeway
Walk up this bridge for a quieter photo spot above the noise! The views of Michigan ave and lake Michigan from here are awesome (& it's free!)
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The Art Institute of Chicago
One of the most well-known art museums in the country, the art institute is home to a plethora of historic, contemporary, and rotating exhibitions. Check their calendar to see what might be of interest during your visit.
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Lake Michigan Sunset Cruise in Chicago
After an afternoon indoors, head out on the lake with this sunset cruise. Absolutely one of my favorite things to do by far!!!
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The Chicago Theatre
A perfect photo op spot in the evening as the sun is going down!
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Pops for Champagne
A popular champagne bar, this is a great spot to cheers to your trip in Chicago!
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Bavette's Bar & Boeuf
Known as one of the best steakhouses, if not THE best, in the city. This is an upscale dinner spot that must be tried on your next visit. Get their oysters as a starter and of course one of their delicious cuts of meat.
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Day 3

Goddess and the Baker, Wacker & LaSalle
One of my favorites to sit and hang out with a pastry and a cup of coffee!
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Garrett Popcorn Shops
Garrett's is a staple snack in Chi-town. Definitely get their mix, a little sweet, a little salty, to satisfy your cravings.
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Harold Washington Library Center, Chicago Public Library
Head up to the hidden winter garden on the top floor of the Washington Public Library for views of the Sears/Willis tower and a serene escape.
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Chicago Cultural Center
Go in and see the beautiful murals and tiffany dome of the Chicago cultural center.
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Wrigley Field
Catch a Cubs game for a taste of the real Chicago energy. Huge sports "town!" you better be singing gooo cubbies go!
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The Salt Shed
Check the schedule ahead of your visit to see what bands are playing! This is a super fun venue that once was the Morton salt processing factory, but has become a groovy live music and concert spot.
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Day 4

m.henry
Start day four in Ukrainian village/Edgewater at this adorable brunch spot. Their coffee is bottomless and their french toast is easily my favorite thing on the menu.
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North Avenue Beach
On your way back toward the city, a stop at North Avenue is required for one of the best skyline views in the whole city.
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Oak Street Beach
If you are walking back south, you'll definitely pass by Oak Street Beach. Known by locals as the ledge, it is a popular spot for sunning and swimming in the summer.
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Day 5

The Wrigley Building
On your way over to the Willis tower, stop to admire some prime Chicago architecture on Michigan ave. Snap some photos, this makes for a beautiful background.
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Willis Tower
Go out with a bang, ascending the Willis tower for views over all of downtown. Step out onto the ledge if you dare!
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Skydeck - Willis Tower Admission
Buy a ticket ahead of time to save and skip the line!
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Girl & The Goat
Head to the west loop for dinner at this trendy, cozy restaurant. The chicken skewers are so succulent and flavorful.
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Where to Stay

Hampton Inn & Suites Chicago-Downtown
An easy, more affordable stay in the heart of the city! The rooms here are spacious and the staff is particularly kind! The free breakfast buffet in the morning is also awesome for a bite and caffeine fix.
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Loews Chicago Hotel
This fancy, upscale hotel is perfect for travelers looking for onsite amenities and spacious, airy rooms.
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The Royal Sonesta Chicago Downtown
I was obsessssed with this hotel downtown. It is right on the riverwalk, my room was HUGE and even had its own personal fitness area! So clean, and the decor was perfectly Chicago inspired.
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Warwick Allerton - Chicago
Right on Mag Mile, the rooms here are modest but definitely have a great location.
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