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Cheap round-trip flights to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

View real-time flight reviews to Chicago from customers like you

Sep 21, 2018

Coffee on 2 leg grt

Sep 21, 2018

Nice flight attendants

Sep 20, 2018

Surprised by American staff, pleasantly

Sep 20, 2018

For the price, couldn't have been better. I hear a lot of poor reviews of Spirit but my personal experience was great.

Sep 20, 2018

On time. No problems

Sep 20, 2018

My luggage did not arrive

Sep 20, 2018

Good economy price

Sep 20, 2018

Everyone should be allowed one free carry on otherwise it was a great trip

Sep 20, 2018

Terrible boarding process; takes too long.. .

Sep 20, 2018

LOVE LOVE LOVE DELTA

Cheap Flights to Chicago

Big time sports, top summer fun and artistic delights, Chicago wears its attractions well. And with more than 50 million people visiting the city each year, it’s clear that it’s got broad appeal.


When to Book Flights to Chicago

Summer is undoubtedly the best time to visit Chicago. With beaches along the lake front busy with people and festivals taking place in parks, the city really feels alive. Of course, you’ll need to book plane tickets to Chicago early and expect accommodation to be more expensive, but it’s worth it to experience the city at its best.

In the winter, the city can be freezing cold and with a much smaller choice of things to do. The temperatures plunge from about November onwards and spring doesn’t rear its head until March or April. However, flights and hotels are much cheaper at this time.

Whatever time of year you visit, bring warm clothes as even in the summer it can get a little chilly with cold winds coming in off the lake.


How to Find the Best Flight Deals to Chicago

You can use Orbitz flight search tools to help you to find the biggest choice of Cheap Flights to Chicago.

Use the ‘Nearby Airports’ option, located under the departure and arrival airport boxes. This lets you explore deals available from alternative cities, as well as to both of Chicago’s main airports.

Another top tip is to be flexible on the dates. Click the ‘My Dates Are Flexible’ box when making your search to browse the cheapest flights on other days.

You can also filter and sort your options on the left-hand side of the results page and by using the ‘Show Options’ drop-down.


US Departures to Chicago

There are numeroUS Departures to Chicago from multiple US destinations.

These include:


Main Airports in Chicago

Most flights to Chicago go through Chicago O’Hare International Airport, one of the world’s busiest by plane and passenger traffic. However, Chicago Midway also offers a big range of inbound and outbound Chicago flights to multiple US destinations.

O’Hare is located around 17 miles from the city, with transport options including buses, trains and rental cars.

Midway is located a little closer to the center, at just 10 miles from downtown. You can use the Transit Authority Orange Line to get to city center destinations easily and quickly.


Which Airlines Fly to Chicago?

Direct flights to Chicago are available with a number of different carriers.

These include:

  • American Airlines
  • Southwest
  • Spirit
  • United
  • Virgin America
  • JetBlue
  • Delta

How to Get Around in Chicago

Renting a car from the airport is a good idea if you’re staying in areas outside of the city. However, if you’re going to be based in or around the center for the duration of your stay, it might not be the best idea. Driving in Chicago can be a real hassle, with gridlock often being an issue and parking hard to come by. Bad weather in the winter months only adds to the problem.

Public transport is a good way of seeing the city, including most of the major attractions. Use the Chicago Regional Transport Authority site to plan your journeys online – because the city is laid out in blocks, it’s usually easy to navigate your way around.


What Are the Must-Sees in Chicago?

As one of the biggest cities in the US, Chicago has plenty to see and do. It’s a city with a big arts, theatre and comedy scene so try and take in a show.

The Adler Planetarium features interactive exhibits and you can learn historical lessons at the DuSable Museum of African American History.

With several major sports teams in the city, you can rarely avoid talk of the big game so why not book tickets and take it in first hand? Or if you’re feeling more active, there is ice skating and exhibitions in Millennium Park.

For the best views of the city, head up to the viewing deck of one of Chicago’s many skyscrapers.


Tips for Traveling in Chicago

O’Hare airport is aging, and also huge. Which can make it tricky to get around. Leave plenty of time to get to your flight and expect delays, as they’re pretty common, especially when the weather is bad.

If you’re planning on visiting in winter, be aware that getting around can be tricky, and with freezing temperatures and bitter winds, you’ll need to wrap up very warm.

Chicago When to Go

Come summer, Chicagoans head to the beaches, parks, and festivals along Lake Michigan. A chill often lingers in the air in early summer, while late summer can be muggy. Regardless of the season, pack layers, as weather can fluctuate greatly. Summer also brings spikes in hotel rates.

Fall is pleasant until mid-November, when temperatures plunge, and spring doesn’t get reliably comfortable until late April. Anytime between May and November, you’ll be able to combine season-less indoor attractions with the convivial appeal of the outdoors at the lakefront, on Chicago River boats, and milling around Millennium Park.

Weather and prices are tradeoffs in Chicago. In January and February, the “hawk” (a local term for the harsh wind off Lake Michigan) sweeps down Michigan Avenue, and snow buries the streets. But hotel rates are bargain basement and attractions uncrowded.

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*Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from January through December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.