Cheap Flights to Chicago

A Traveler’s Guide to Chicago

In the colorful words of the celebrated American journalist H.L. Mencken, "I give you Chicago. It is not London and Harvard. It is not Paris and buttermilk. It is American in every chitling and sparerib. It is alive from snout to tail." So, what are you waiting for? Book plane tickets to Chicago for a true-blue American experience.

What to See?

From mouth-watering cuisine, late-night shenanigans to cultural musts, there are a lot of things and places that you need to experience on your trip to Chicago. Once you have booked your flight tickets to Chicago start making a list of things to experience as it will be impossible to visit all the places within a short time. To help you out, we have put together a checklist of the top 5 activities that need to be on your bucket list when you’re in Chicago. So, be prepared to drench yourself in the culture of Chicago.

Architecture Tour Cruises

Chicago’s architecture is a sight to behold. An architectural tour along the Chicago River needs to be on the top of your bucket list. A cruise tour is one of the best ways to explore the famed architecture of Chicago. The Chicago Architecture Foundation has a team of certified volunteers who guide visitors throughout the tour and talk about the history behind the monuments. Hop on to the Chicago’s First Lady from its docking station, which is situated on the gorgeous Chicago Riverwalk for the 90-minute tour ride. There is also a full-service bar inside the boat. You can bring food if you don’t feel like purchasing the munchies on board.

Willis Tower Skydeck

Want to see the city from a height of 1353 feet? You need to visit the Willis Tower Skydeck, which is the second tallest building in the US. Step onto the ledge and look down at the gorgeous view of Chicago under your feet. You can climb up to 103 floors and see up to 50 miles! Don’t like standing in a queue? You can visit the deck at night.

"G" Dog

You have to try out the Chicago style hot dog at Hot “G” Dog. The hot dogs are super delicious and different from the standard hotdogs that you get across the United States. Arrive with an appetite and try out the sausages made from alligator or goat meat, with a side of duck fat fries.

Uno Pizzeria & Grill

The infamous Chicago Deep Dish Pizza is a place that you must visit on your trip to Chicago. Started in 1943, Uno Pizzeria & Grill is the place where Chicago’s first deep dish pizza was served. There are several Uno Pizzeria franchises across the country. However, if you want to visit the original non-franchise versions, head to the River North neighborhood. Do try their delectable mozzarella deep dish pizza among the different options available.

Art Institute of Chicago

True to its name, the Art Institute of Chicago is home to the permanent collection of more than 300,000 artworks. The masterpieces on display come from different eras-from Georges Seurat to Andy Warhol-they have it all! Be sure to check out the Medieval armory. Located past the renaissance era paintings on the second floor, it has an impressive collection of swords, suits of armor, and crossbows.

How to Reach Chicago?

• Flights - You can take cheap flights to Chicago’s 5 different airports namely, Chicago O’Hare International, Chicago Midway, Chicago DuPage County, Chicago Pal-Waukee and Chicago Rockford
• Train - You can take a train to Chicago Union Station
• You can also take a bus if you are coming from another city in the US. Several bus operators run services every day of the week to and from Chicago.

Best Time to Visit

The best time to buy round trip flights to Chicago is in the spring, which is from April and June. You can also visit Chicago during the peak fall season between September and October.

Find Cheap Fares

Find cheap flights from Chicago and back by logging onto fly.com. Our fares are calculated after comparing 500+ airlines and travel sites to give you the best deals on round trips to Chicago. If you are a bit flexible on dates, then use our fare calendar to help you decide from a series of dates on which you will find cheap airplane tickets to Chicago and back. We also offer fantastic deals on last-minute flights from Chicago and back. Click on ‘Today’s Best Fares' tab on our site to find out more. Also, find cheap weekend flights from Chicago with fly.com.