Seven Tips on Finding Cheap Flights to Chicago O’Hare (ORD)

Follow these 7 tips from Hopper to find cheap flights to Chicago and you could save up to $630 per round-trip ticket!

Patrick Surry - Jan. 27, 2015

Home to Chicago-style hot dogs, deep-dish pizza, the Chicago Cubs and a sketch comedy scene that helped sparked several comedians’ careers, Chicago offers visitors a melting pot of cultural gems. And its Midwestern mentality make it a lot more approachable compared to the New Yorks and Los Angeleses of the world. With its infinite amount of attractions — Lake Michigan, the ferris wheel at Navy Pier, Willis Tower Skydeck (aka Sears Tower) and Second City comedy club, to name a few — visitors will need to plan accordingly. Plus, travelers will want to save up so they can spend more money on deep-dish pizza. Here are six tips that can save travelers up to $630 when looking for cheap flights to Chicago.

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Photo by Jamie In Bytown via Flickr.

1. The cheapest time to book a flight to Chicago is 15 days in advance, saving up to $200

Book your flight to Chicago at least two weeks in advance because tickets can rise up to $200 closer to the departure date. Plus, getting a ticket for one of the comedy shows or concerts will be easier the earlier you start planning.

2. The cheapest day to fly to Chicago is on a Friday, saving up to $184

Chicago is the perfect weekend getaway with a central location that makes it easy to fly from almost anywhere in the United States. Book your ticket for a Friday departure and you can save up to $184, while still making it in time for happy hour specials. Order a brandy-based Chicago Cocktail to start off the weekend right and be thankful that airlines charge leisure travelers less than business travelers.

Check out Hopper's travel section on Chicago to find tons of ideas on how to spend your weekend in the Windy City!

3. Save up to $175 by returning on a Sunday

Arriving on a Friday and leaving on a Sunday would be hard to do because of all the attractions in Chicago, but travelers can save an additional $175 if they do so. That’s just enough time to get in a baseball game or tour of the city’s famous architecture. Make sure to grab a Chicago-style hot dog at some point during your travels. The poppy seed bun and pickles make it a delicious meal.

4. The cheapest day to buy a flight to Chicago is on a Tuesday, saving up to $31

Instead of YouTubing videos of cats making funny faces, spend your busy work week buying a ticket to Chicago. Travelers can save up to $31 just by making the purchase on a Tuesday. That’s enough money for a ticket to see a live comedy act, which — if you’re lucky — may even include a funny cat or two.

5. The cheapest time to fly to Chicago is in January, saving up to $40

It’s no surprise that tickets to Chicago are cheaper in January. Temperatures sometimes drop below zero degrees, but the snow in the Windy City can seem magical to those who don’t get to experience it in warmer, seasonless climates. Plus, less tourists means more tickets are available to see your favorite band or one of the many Broadway shows that tour the city. Just don’t expect long walks on Lake Michigan or pleasant boat rides on the river.

6. Use Hopper’s When to Fly and Buy Reports to check if you’re getting a good deal

Travelers can also visit Hopper.com to double check whether or not they are getting a good deal. Simply enter the airports you will fly in and out of, and the When to Fly and Buy Reports will tell you the best ticket prices, airlines and day of week to travel.

7. Take a look at Hopper’s Airline Fees Calculator to get the real cost of your ticket

Think you may need an additional carry-on bag to bring that winter coat? Perhaps an in-flight meal so you’re ready for sightseeing straight from the plane? Maybe you just fancy a little bit of extra leg room, or some drinks for the ride. Whatever additional services you may require from your airline on the way to Chicago this year, be sure to check out Hopper’s Airline Fees Calculator, which provides a detailed visual breakdown of all the associated costs and charges.

Get up-to-date information on finding cheap flights to Chicago using Hopper's interactive flight tools.

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