Cheap Flights to Chicago
Bargain flights to Chicago are a good way to get you into a city that is full of art, culture, and history.
Flights to Chicago
Generally, flights to Chicago land at O'Hare International Airport, although Midway International Airport is gaining popularity. Midway International is located just 10 miles from the downtown center, and there are shuttle buses to hotels as well as the Transit Authority's Orange Line. Chicago flights that land at O'Hare International Airport put you about 17 miles northwest of the city, and transportation options include regional trains and buses, car rentals, and transit lines. Music in the terminals is listed and you can log into the airport website to find out exactly what you were hearing! Just be aware that if you do this from the airport, the available Wi-Fi is charged at $6.95 a day.
The term "Windy City" may actually refer to politicians' speeches, but that doesn't change the fact that the weather is often blustery. Whenever you visit, you will want to keep a jacket on hand for the lake breezes. Weather becomes nasty between November and March, especially in January, when temperatures drop to 24°F (-4°C), and are emphasized by that ubiquitous wind, as well as snow! Plan for indoor activities if you visit during this time period! You'll probably prefer the weather between April and October, when everyone rushes outside. During the peak tourist season, temperatures hover around 85°F (29°C).
Getting Around Chicago
Driving in downtown Chicago is a hassle best avoided. Traffic is overwhelming, pedestrians often don't follow the rules of the road, parking spaces are expensive, and tickets and towing are strict for violations, especially in the snow! The best way to get around Chicago is public transit. With several different agencies in the Chicago area all overseen by the RTA (Regional Transportation Authority), you can plan trips online with their planner. Once your Chicago flights have landed, navigating the city is easy. The city is consistent in street numbering and block lengths and organized on a grid that is easy to get used to. There are, however, some notable exceptions, avenues like Milwaukee and Ogden that go diagonally or meander through the city.
Chicago is a bustling city, with many things to do and see within its city limits. Explore the arts, the night life, and even some natural areas to keep busy. Below are some suggestions to get you started:
- The Adler Planetarium, with astronomy shows and neat interactive space exhibits.
- DuSable Museum of African American History, with exhibits of the history and achievements of people of African descent in Chicago.
- Rogers Park beach, with miles of sand to remind you that you're on the largest freshwater lake entirely in the United States.
- Shedd Aquarium, with exhibits that cover the Caribbean and the Pacific Northwestern United States.
- Milennium Park, with ice skating, cultural programs, and exhibitions in the new Chicago town square.
Best Anytime fares to Chicago
Cheap round-trip flights to Chicago
|New York||Chicago||Wed, Sep 10 - Wed, Sep 17||Spirit Airlines||$185|
|Los Angeles||Chicago||Mon, Aug 25 - Tue, Aug 26||American Airlines||$213|
|Washington DC||Chicago||Mon, Sep 22 - Thu, Sep 25||Frontier Airlines||$105|
|Denver||Chicago||Tue, Aug 19 - Wed, Aug 27||Spirit Airlines||$125|
|Boston||Chicago||Sat, Sep 20 - Tue, Sep 23||Spirit Airlines||$155|
|San Francisco||Chicago||Thu, Sep 4 - Fri, Sep 5||Virgin America||$265|
|Minneapolis||Chicago||Tue, Sep 9 - Tue, Sep 16||Spirit Airlines||$79|
|Seattle||Chicago||Sat, Sep 13 - Tue, Sep 23||Frontier Airlines||$310|
|Philadelphia||Chicago||Tue, Aug 26 - Wed, Sep 3||jetBlue||$294|
|Newark||Chicago||Tue, Aug 26 - Fri, Sep 5||jetBlue||$226|
|Portland||Chicago||Wed, Sep 10 - Sat, Sep 13||Spirit Airlines||$225|
|Atlanta||Chicago||Tue, Aug 19 - Wed, Aug 20||AirTran Airways||$237|
Best weekend fares to Chicago
Best weekend fares to Chicago
|New York||Chicago||Thu, Sep 11 - Sat, Sep 13||Spirit Airlines||$195|
|Los Angeles||Chicago||Fri, Sep 12 - Sat, Sep 13||Delta Air Lines||$237|
|Washington DC||Chicago||Fri, Sep 26 - Sat, Sep 27||Frontier Airlines||$125|
|Denver||Chicago||Sat, Aug 30 - Mon, Sep 1||Spirit Airlines||$145|
|Boston||Chicago||Sat, Sep 6 - Mon, Sep 8||Spirit Airlines||$170|
|San Francisco||Chicago||Fri, Sep 5 - Sun, Sep 7||American Airlines||$285|
|Minneapolis||Chicago||Thu, Sep 11 - Sat, Sep 13||Spirit Airlines||$92|
|Seattle||Chicago||Fri, Sep 12 - Sat, Sep 13||Frontier Airlines||$299|
|Philadelphia||Chicago||Thu, Sep 25 - Sat, Sep 27||United Airlines||$305|
|Newark||Chicago||Thu, Sep 11 - Sat, Sep 13||jetBlue||$258|
|Portland||Chicago||Thu, Sep 11 - Sat, Sep 13||Spirit Airlines||$240|
|Atlanta||Chicago||Thu, Sep 4 - Sat, Sep 6||Spirit Airlines||$282|
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.