Chicago Travel Guide

Chicago Travel Guide

Chicago is one of those cities where you have to visit at least once during your lifetime. Commonly known as Chi-Town or The Windy City, Chicago is famously known for their food, art, and wind. Their deep dish pizza and hot dogs (don't you dare put ketchup on that!) cannot be beat and you can feel the art vibe flowing through the streets and buildings with top-notch broadway and comedy shows as well as a playground for outdoor sculptures like Cloud Gate!  

In this Chicago Travel Guide, I'll be covering When to Visit ChicagoWhere to StayFood & Drink, Things to Do & See & the Best Photography Spots in Chicago.

Giordano's Deep Dish Pizza - Chicago Travel Guide

When to Visit Chicago

When To Visit Chicago

Best Time Overall

Visit Chicago in the Fall (September - October) or in Spring (April - May).

The temperatures are warmer and the hotel prices are cheaper.

Cheapest Time To Visit

Winter (November - March)

Prepare for the cold and windy weather. 

Best Weather

Summer (June - August)

You'll have to share the heat with many other tourists. 

Where To Stay

Hyatt Chicago Magnificent Mile

If you want to stay near major sights and attractions, definitely check out The Loop and Magnificent Mile. 


The Loop (Art Institute of Chicago, Millennium Park [The Bean])

Hyatt Centric The Loop Chicago
Kimpton Burnham Hotel

Magnificent Mile (360 Chicago, Navy Pier)

Hyatt Chicago Magnificent Mile

Food & Drink

Giordano's Deep Dish Pizza

Au Cheval Burger

Pizza at Pixano's (Deep Dish)

Au Cheval (burger) Open from 11:00AM - 1:00AM. Waits can be long (3.5 hours) but

Bang Bang Pie and Biscuits (breakfast & dessert)

Little Goat (breakfast)

Do-Rite Donuts & Chicken (lunch & dessert)

Yolk (brunch)

Wildberry Pancakes and Cafe (brunch)

Lou Malnati’s Pizzeria (deep dish)

Giordano's (deep dish)

Portillo's Hot Dogs & Barnelli's Pasta Bowl

The Girl and the Goat (dinner) -Reservation are months in advance

The Doughnut Vault (dessert) 

Stan's Donuts and Coffee (dessert)

Glazed & Infused (dessert)

Things To Do & See in Chicago

The Field Museum


The Field Museum - Sue the Dinosaur

Art Institute of Chicago - Andy Warhol

Big Bus Tour - An easy and convenient way to see Chicago. 

Millennium Park 

Cloud Gate (The Bean)
Art Institute of Chicago  (American Gothic (pitch fork) Night Hawks)
Crown Fountain - Two interactive video sculptures of a man and women. Perfect for a hot day to get soaked.

360 Chicago Observatory Deck - Chicago Tilt (formally known as the John Hancock Observatory)

Navy Pier (lake and river cruise)

The Field Museum (dinosaurs largest t rex)

Willis Tower (formally known as the Sears Tower) - Sunset Skyline View

The Second City (Improv Comedy)

Chicago CityPass

Theater District

Garfield Park Conservatory - Indoor plants 

Lincoln Park - zoo is free/hicago history museum 

Museum of Contemporary Art

Oak Park - Birthplace of Ernest Hemingway

Best Photography Spots in Chicago

Cloud Gate - The Bean - Chicago Travel Guide

Chicago Theater - Beautiful building that is great for a long exposure shot at night 

Navy Pier - Capture Chicago's fun-filled pier complete with a ferris wheel! 

Shedd Aquarium - Beside getting some cool aquatic photos, there are a few spots along Shedd that has a view of Chicago's Skyline.

Art Institute of Chicago - The building is photogenic inside and out.

Cloud Gate (The Bean) - You definitely can't come to Chicago without photographing its famous landmark!