• About
  • Home
  • TRAVEL
    • California
      • Big Sur
        • A Complete Guide to Visiting Big Sur
        • A Complete Guide to Visiting Carmel by The Sea
      • Joshua Tree
        • A Complete Guide on Day Tripping to Joshua Tree
        • Best Things to Do in Pioneertown California: A Complete Guide
      • Los Angeles
        • A Complete Guide to Visting Catalina Island
        • 20 of The Best Photo Spots in Los Angeles
      • Palm Springs
        • The Ultimate Palm Springs Weekend Travel Guide
        • 20 Best Instagram Spots in Palm Springs: A Complete Guide
      • San Juan Capistrano
      • San Diego
        • The Ultimate San Diego Travel Guide: written by a local
        • The Best Pumpkin Patches in San Diego
        • The Best Photo Spots in San Diego: A Photography Guide
        • The Insider’s Guide to Balboa Park
        • Best Things to Do in San Diego
        • The 25 Best Coffee Shops in San Diego, California
      • Santa Barbara
        • Best Photo Spots in Santa Barbara, California
      • San Francisco
        • 18 of The Best Photo Spots in San Francisco
        • Visiting Sausalito: a Perfect Day Trip from San Francisco
      • Yosemite
        • A Complete Guide to Visiting Yosemite National Park
    • Europe
      • Italy
        • A First Timer’s Travel Guide to the Amalfi Coast
        • A First Timer’s Guide to Visiting Florence, Italy
        • An Ultimate Guide to the Top Sights in Rome
      • 4 Days in Paris Itinerary
      • An Ultimate City Guide: Fun Things to Do in Barcelona
      • 2 Days in Seville: a Complete Seville Itinerary
      • First Timer’s Travel Guide to London
      • 2 Days in Amsterdam Itinerary: A First Timer’s Guide
    • Hawaii
      • A Complete Travel Guide to Visiting Maui, Hawaii
      • A First Timer’s Guide to The Road to Hana in Maui, Hawaii
      • My Experience Traveling to Hawaii during Covid
      • Everything You Need to Know Before Visiting Queens Bath
      • The Ultimate 5 Day Kauai Itinerary: a travel guide
      • Best Oahu Instagram Spots: a Photography Guide
      • Hoomaluhia Botanical Garden
      • The Best North Shore Oahu Beaches to Visit
      • Most Beautiful Places in Kauai: Best Photo Spots
    • New York
      • 36 Must See Places in New York: written by a local
      • A Guide to the Best Central Park Photo Spots
      • A Local’s Guide to Visiting Montauk New York
      • 15 Christmas Activities in New York: Best Things to Do in December
      • 15 Christmas Activities in New York: Best Things to Do in December
    • Mexico
      • Tulum
        • The Ultimate Tulum Travel Guide
        • The Ultimate Guide to Tulum Instagram Spots
      • What to Pack for Mexico: a Packing List
    • USA
      • The Best 2 Day Zion National Park Itinerary
      • One Day in Bryce Canyon National Park: A Complete Itinerary
      • 17 of The Best Things to Do in Seattle: a First Timer’s Guide
      • A Complete Weekend Travel Guide to Sedona
      • How to Spend 3 Days in Chicago: a Chicago Itinerary
      • A Complete Weekend Guide to Scottsdale Arizona
      • A Complete Weekend to Boston Trip Itinerary
      • The Ultimate Weekend in Charleston Itinerary
      • New Orleans Weekend Travel Guide: Best Things to Do in NOLA
      • The Best Las Vegas Photo Spots Guide
    • Hotels & Resorts
      • Complete Hotel Review: Sands Hotel and Spa in Palm Springs
      • Complete Resort Review: Iberostar Grand Bavaro Punta Cana
    • Travel Tips
      • The Ultimate Packing Guide: 29 Must Have Travel Essentials
      • Best Practices on How to Find Cheap Flights
  • Style + Lifestyle
    • Product Reviews
      • An Honest Dior Saddle Bag Review + How to Style
      • My Honest Review of the Gucci Princetown Mule
      • My Honest Gucci Marmont Shoulder Bag Review + How to Style
      • My Honest Stuart Weitzman 5050 Boot Review + How to Style
      • 5 Reasons Why You Need the Gucci Soho Disco Bag
      • Are Necessaire Products Worth the Hype? A Full Review
      • A Complete Review of SkinCeuticals C E Ferulic Serum
    • Packing Guides
      • Travel Capsule Wardrobe: How to Dress Like A European
      • 35 Airport Outfits: How to Look Effortless while Traveling
      • The Ultimate Packing Guide: 29 Must Have Travel Essentials
      • What to Pack for Hawaii: The Ultimate Hawaii Packing List
      • What to Pack for Italy: a packing list
      • What to Wear in Palm Springs: The Best Packing Guide
      • What to Pack for Mexico: a Packing List
    • Styling Guides
      • 14 Cute Summer Outfits Ideas to Try in 2022
      • 25 of The Best Denim Shorts to Wear this Summer
      • How to Create a Capsule Wardrobe: The Essentials
      • 12 Bodysuits to Shop Now
      • How to Style a Slip Dress
      • 18 Best Straight Leg Jeans and How to Style Them
      • Fall Outfit Ideas: The Best Trends to Try in 2022
      • 28 Best Holiday Outfits: What to Wear this Holiday
    • Photography
      • A Guide to the Best Central Park Photo Spots
      • The Best Photo Spots in San Diego: A Photography Guide
      • Best Photo Spots in Santa Barbara, California
      • A Complete Guide on Day Tripping to Joshua Tree
      • Most Beautiful Places in Kauai: Best Photo Spots
      • 20 of The Best Photo Spots in Los Angeles
      • The Best Las Vegas Photo Spots Guide
      • Best Oahu Instagram Spots: a Photography Guide
      • 18 of The Best Photo Spots in San Francisco
      • The Ultimate Guide to Tulum Instagram Spots
      • How to Edit in Lightroom Classic
      • The Best Photo Editing Apps for your iPhone
    • Lifestyle
      • Christmas Gift Ideas 2022: The Ultimate Holiday Gift Guide
      • Our Boho Mid Century Modern Home Tour in San Diego
      • The 25 Best Coffee Shops in San Diego, California
    • Skincare
      • The Best Summer Skincare + SPF Essentials for Glowing Skin
      • What I’m Purchasing at the Sephora Sale 2022
      • A Complete Review of SkinCeuticals C E Ferulic Serum
      • Vitamin C Serum Benefits: and The Best Ones to Buy
      • Best Skincare Products + How to Layer Correctly
      • Are Necessaire Products Worth the Hype? A Full Review
  • San Diego
    • The Ultimate San Diego Travel Guide: written by a local
    • 20 San Diego Hidden Gems: written by a local
    • An Ultimate Guide to the Best Brunch in San Diego
    • Best Restaurants to Try in San Diego for 2023
    • The Ultimate Guide to San Diego 4th of July 2022
    • A Complete Locals Guide on Things to Do in Balboa Park
    • The 25 Best Coffee Shops in San Diego, California
    • The Best Photo Spots in San Diego: A Photography Guide
    • A Local’s Guide to Coronado Island
    • A Complete Guide to Visiting Carlsbad Flower Fields 2023
    • The Ultimate Guide to San Diego Christmas Activities
    • The Best Pumpkin Patches in San Diego
  • Work With Me
  • Shop
  • Travel
    • california
      • big sur
      • joshua tree
      • los angeles
      • palm springs
      • san diego
      • san francisco
      • santa barbara
      • yosemite
    • europe
      • amsterdam
      • An Ultimate City Guide: Fun Things to Do in Barcelona
      • 2 Days in Seville: a Complete Seville Itinerary
      • italy
        • amalfi coast
        • florence
        • rome
      • london
      • paris
    • hawaii
    • mexico
    • New York
    • usa
      • The Best 2 Day Zion National Park Itinerary
      • arizona
      • boston
      • charleston
      • Chicago
      • new orleans
      • seattle
    • hotels
      • Sands Hotel and Spa in Palm Springs
  • Blog
    • Style
    • photography
    • packing guides
    • product review
    • Lifestyle
    • skincare
  • San Diego
  • Work With Me
  • Shop My Looks

Le Travel Style

by Courtney Delfino • a San Diego based travel + lifestyle blog inspiring you to travel in style

Travel, Travel Guides, USA · Last Updated: September 14, 2022

How to Spend 3 Days in Chicago: a Chicago Itinerary

A full 3 days in Chicago Itinerary

So you only have 3 days in Chicago? Well, that is the perfect amount of time to explore the windy city. Chicago is one of my favorite cities because it has a little something for everyone to enjoy. The people are pure gold, the food is *chefs kiss*, and there are ample things to do in Chicago. In this guide, I’m sharing everything to know before visiting so you can truly enjoy all it has to offer!

Best Time to Visit Chicago

the chicago theatre marquee
sunrise at chicago riverwalk

They don’t call it the windy city for anything! The temperatures in Chicago can drop below zero in the winter so it’s best to travel to Chicago from May-July and September-November. Where the weather is mild and you’ll be able to enjoy walking around the city without freezing. Finally, St. Patricks Day is the most popular time to visit Chicago. The riverwalk turns green to celebrate the occasion and the entire city takes place in the festivities.

Where to Stay in Chicago

the langham chicago lobby
girl in front of window of four seasons Chicago during the day

Chicago has no shortage of beautiful hotels to choose from. If you’re like me and love a little luxury then I highly recommend these two hotels:

  • The Langham Chicago: luxury at its finest with the best views of the riverwalk. Make sure to take advantage of their club access when staying it includes breakfast, lunch, and dinner. The food is incredible.
  • The Four Seasons: the ultimate 5-star hotel with incredible service and the rooms have beautiful views of the lake.

Mid-range hotels:

  • The Pendry: located right across from Millennium Park this hotel is in a prime location.
  • Kimpton Gray Hotel: also located near millennium park this hotel offers packages that include food as well.

Things to Do in Chicago

girl in front of the Chicago bean at millennium park
girl posing in front of red tree at the honeycomb in lincoln park chicago

Millennium Park

Home to the infamous bean, Millennium Park is a must-see for every visitor. The bean sculpture is the most famous landmark in this city and with the Chicago skyline in the background, it makes for the perfect photo op. As you can see, it’s magical to visit during the fall. Finally, because of Covid, it doesn’t open until 8 am now.

Architecture River Cruise

If you’ve seen “My Best Friends Wedding” then you’ll remember when Julia Roberts is dancing with Michael atop the Architecture River Cruise. It’s one of the most popular things to do in Chicago. A must-see for your 3 days in Chicago. There is nothing like admiring architecture from the water. There are ample architecture tours to choose from ranging from 60 minutes to 90 minutes. Linking a popular tour here. Make sure to make reservations in advance.

Walk the Chicago Riverwalk

girl sitting on ledge in front of the Chicago Riverwalk
sunrise at Chicago riverwalk

This 1.25-mile path is located along the river and is a treasured natural amenity for residents and tourists alike. Whether you choose to walk, run, or just sit on a bench and admire you’ll experience the prettiest views of the city. It’s open from 6 am – 11 pm and is best experienced in the early morning while the city is still sleeping. Furthermore, you’ll recognize this spot from many movies including one of my personal favorites, While you were sleeping.

Lincoln Park

girl in front of fall foliage holding a leaf
girl in front of honeycomb structure in Lincoln Park during fall

Lincoln Park is Chicago’s largest park bordering the most affluent neighborhoods in the city. It’s an oasis to the locals from the bustling city of Chicago. This park is home to the insta-famous Honeycomb and the Lincoln Park Zoo. When visiting, you’ll be surrounded by nature while admiring the skyline from afar. Grab your walking shoes to explore this beautiful part of the city. It’s especially pretty to visit in the fall to witness the changing leaves against the cityscape.

Skydeck Chicago

View this post on Instagram

A post shared by Talia | San Diego + Travel (@travelwithtalia)

Explore Chicago from above on the 103rd floor of the Sears Tower. With clear observation boxes, you’ll be looking down on the entire city (and be able to see 4 states). It’s most definitely an experience everyone needs to try when visiting.

The Chicago Theatre

the Chicago theatre marquee
girl in blue dress posing in front of the Chicago Theatre Marquee

An icon! The Chicago Theatre rivals “the bean” for the most photographed part of the city. This legend was built in 1921 and was America’s first large movie palace. Even if you’re not going to a show, you need to visit the famous marquee. Click here for a show schedule.

The Magnificent Mile

If you’re an avid shopper then The Magnificent Mile is the place for you. This street spans one mile of high-end luxury stores, beautiful architecture, and top-notch eateries. It’s the perfect place to spend an afternoon and grab lunch when you only have 3 days in Chicago.

Visit Milton Lee Olive Park

Image gallery image

Located close by to Navy Pier is Milton Lee Olive Park. It’s lesser known spot overlooking Lake Michigan featuring stunning views of the skyline. Finally, it’s a secluded spot to the city often with runners and locals taking their daily walk.

Other things to do in Chicago if you have time:

  • Visit Navy Pier
  • Catch a ball game at Wrigley Field
  • 360 Chicago Observation Deck
  • Garfield Park Conservatory
  • Admire the architecture at the University of Chicago
  • Visit North Avenue Beach
  • Check out the Chicago Water Tower
  • Check out the Museum of Science
  • Beautiful views from the Willis Tower

Where to Eat in Chicago

interior of three arts cafe
Three Arts Cafe
Adorn Restaurant Plating featuring poutine and pasta
Adorn at The Four Seasons
  • Three Arts Cafe ($$$$): Did you really visit Chicago if you didn’t go to Three Arts Cafe? The prettiest restaurant in Chicago. Located inside the Restoration Hardware store this cafe is heaven. Don’t sleep on the burger, the best one I’ve ever had in my life!
  • Beatnik on the River ($$$): amazing views of the riverwalk and delicious Mediterranean-inspired foods.
  • Adorn ($$$$): located in the Four Season Hotel, Chef Jonathon Sawyer is cooking up award-winning dishes featuring global-inspired cuisine. Get the poutine and thank me later!
  • Pequod’s ($$): the locals love this spot for the most famous Chicago dish, deep-dish pizza. Being from New York, I’m a hard one to judge but this was surprisingly good. Chicago deep dish pizza is not your average pizza and reminds me more of a casserole dish. But nonetheless, still tasty!
  • Portillo’s ($): when visiting Chicago you NEED to get a famous Chicago dog. Portillos’s is the most famous spot with locations all around the city. What makes Chicago dogs special is its poppy seed bun.
  • Do-Rite Donuts & Chicken ($)
  • Girl & The Goat ($$$)
Pequods Deep Dish Pizza Chicago
Pequods
Plating of Beatnik on The River Chicago
Beatnik on The River

What to Pack for Chicago

While all opinions and recommendations are always my own, the content on this blog post contains affiliate links for products I use and love. This means I get a small commission (at no additional cost to you) if you make a purchase after clicking one of these links. As always, I am so thankful for your support so I can continue to offer free resources!

  • If you’re traveling during the colder months make sure to have a warm coat. I’m talking about a puffer jacket. We all want to look cute but when walking around Chicago I highly suggest this puffer coat.
  • Warm socks to keep your feet warm
  • A comfortable but cute pair of booties. I love these chic ones, they’re comfortable for walking!
  • A warm beanie
  • A good scarf
  • My favorite leather leggings that pair nicely with the booties

Thank you for reading my 3 day Chicago itinerary. I hope you have a fabulous time exploring the windy city. If you need more help packing you don’t want to miss my “22 Travel Essentials for your next trip” post. Enjoy your trip!

pin this post for later

collage of Chicago city views
how to spend 3 days in chicago

XX, Courtney

In: Travel, Travel Guides, USA · Tagged: chicaco, travel, usa travel

You’ll Also Love

Moms Pies in Julian California12 Amazing Things to Do in Julian California
The Perfect Amsterdam 2-Day Itinerary: A First Timer’s Guide
The Ultimate Paris Packing List for Every Season

Leave a Reply

Your email address will not be published. Required fields are marked *

Next Post >

The Best Pumpkin Patches in San Diego

  • Privacy Policy
  • Disclaimer
  • Terms
  • Work With Me

Copyright © 2023 Le Travel Style · Theme by 17th Avenue