Cheap Flights from Chicago
Flights from Chicago
Pay no Orbitz booking fees on single-carrier flights from Chicago that are reserved online. That's good on flight-only reservations that originate from the U.S., Canada, Mexico or the Caribbean. Removing fees is just one way we can ensure cheap flights from Chicago.
Miles? Yes. Window? Yes. Cheap flights from Chicago on Orbitz? Yes.
- Add your frequent flier number when you book a cheap flight from Chicago on Orbitz, and accumulate miles on applicable flights.
- Choose your seats on flights from Chicago — aisle or window, front or back.
- Get airfare alerts for flights from Chicago. Set your target price, destination, and travel dates, and we'll send you an alert if we find cheap flights from Chicago that meet or beat your target price. Orbitz Deals E-mail can help you catch discount flights from Chicago, too.
An entire support team for your flights from Chicago
When you book your cheap flights from Chicago on Orbitz, you get free, real-time trip updates sent to your mobile phone about delays and other events that could impact your travel. Choose to have your alerts sent to up to six others, such as the person picking you up from the airport in Chicago when you return.
Need to change your cheap flights from Chicago?
You don't have to call to change your flights from Chicago. You can do that yourself online. We'll let you know if there's part of your airfare that can be put toward a future flight from Chicago. Travel should be a pleasure, so that's why we strive to get you the best deal on cheap flights from Chicago and deliver the support you deserve.
Best Anytime fares from Chicago
Cheap round-trip flights from Chicago
|Chicago||Las Vegas||Wed, Jan 22 - Wed, Jan 29||Spirit Airlines||$208|
|Chicago||Cancun||Sun, Feb 2 - Tue, Feb 4||American Airlines||$252|
|Chicago||Vallarta||Sat, Feb 8 - Tue, Feb 11||AeroMexico||$257|
|Chicago||Phoenix||Tue, Dec 17 - Thu, Dec 26||Spirit Airlines||$138|
|Chicago||New York||Wed, Jan 22 - Wed, Jan 29||JetBlue Airways||$148|
|Chicago||Orlando||Wed, Jan 29 - Sun, Feb 2||Spirit Airlines||$246|
|Chicago||Honolulu||Sun, Feb 2 - Wed, Feb 5||US Airways||$633|
|Chicago||Los Angeles||Tue, Jan 14 - Wed, Jan 15||Spirit Airlines||$188|
|Chicago||Mexico City||Fri, Jan 24 - Fri, Feb 21||United Airlines||$261|
|Chicago||Denver||Sun, Feb 9 - Wed, Feb 12||Frontier Airlines||$138|
|Chicago||San Juan||Wed, Jan 22 - Thu, Jan 30||United Airlines||$297|
|Chicago||Maui (Island of Maui)||Tue, Jan 28 - Tue, Feb 4||United Airlines||$672|
Best weekend fares from Chicago
Best weekend fares to Chicago
|Chicago||Las Vegas||Fri, Jan 3 - Mon, Jan 6||Spirit Airlines||$208|
|Chicago||Cancun||Fri, Jan 31 - Sun, Feb 2||United Airlines||$350|
|Chicago||Vallarta||Thu, Jan 9 - Mon, Jan 13||AeroMexico||$466|
|Chicago||Phoenix||Fri, Dec 13 - Mon, Dec 16||Spirit Airlines||$138|
|Chicago||New York||Thu, Jan 23 - Mon, Jan 27||Spirit Airlines||$168|
|Chicago||Orlando||Thu, Jan 30 - Mon, Feb 3||Spirit Airlines||$246|
|Chicago||Honolulu||Thu, Jan 30 - Mon, Feb 3||US Airways||$633|
|Chicago||Los Angeles||Thu, Jan 16 - Sat, Jan 18||Spirit Airlines||$213|
|Chicago||Mexico City||Thu, Feb 6 - Sun, Feb 9||United Airlines||$261|
|Chicago||Denver||Sat, Jan 25 - Mon, Jan 27||Spirit Airlines||$148|
|Chicago||San Juan||Fri, Feb 7 - Mon, Feb 10||United Airlines||$362|
|Chicago||Maui (Island of Maui)||Thu, Feb 6 - Sun, Feb 9||Alaska Airlines||$852|
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. 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.