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.
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.
Best Anytime fares to Chicago
Cheap round-trip flights to Chicago
|New York||Chicago||Wed, Dec 3 - Tue, Dec 9||Frontier Airlines||$167|
|Los Angeles||Chicago||Wed, Dec 10 - Wed, Dec 17||United Airlines||$253|
|Washington DC||Chicago||Wed, Dec 10 - Wed, Dec 17||Frontier Airlines||$105|
|Denver||Chicago||Tue, Dec 9 - Tue, Jan 6||Spirit Airlines||$137|
|Boston||Chicago||Tue, Dec 16 - Tue, Jan 6||United Airlines||$161|
|San Francisco||Chicago||Tue, Dec 2 - Wed, Dec 3||United Airlines||$254|
|Minneapolis||Chicago||Tue, Dec 9 - Wed, Dec 10||Spirit Airlines||$81|
|Seattle||Chicago||Sat, Nov 15 - Wed, Nov 19||Frontier Airlines||$289|
|Philadelphia||Chicago||Mon, Nov 24 - Fri, Nov 28||US Airways||$227|
|Newark||Chicago||Wed, Dec 3 - Sat, Dec 6||United Airlines||$219|
|Portland||Chicago||Thu, Oct 30 - Fri, Oct 31||Spirit Airlines||$147|
|Atlanta||Chicago||Tue, Nov 18 - Thu, Nov 20||Frontier Airlines||$105|
Best weekend fares to Chicago
Best weekend fares to Chicago
|New York||Chicago||Thu, Dec 4 - Sat, Dec 6||Spirit Airlines||$177|
|Los Angeles||Chicago||Fri, Oct 31 - Sat, Nov 1||Spirit Airlines||$251|
|Washington DC||Chicago||Thu, Nov 13 - Sat, Nov 15||Frontier Airlines||$105|
|Denver||Chicago||Sat, Dec 6 - Mon, Dec 8||Spirit Airlines||$137|
|Boston||Chicago||Fri, Oct 31 - Sat, Nov 1||Spirit Airlines||$119|
|San Francisco||Chicago||Thu, Dec 4 - Sat, Dec 6||Virgin America||$255|
|Minneapolis||Chicago||Thu, Dec 4 - Mon, Dec 8||Spirit Airlines||$81|
|Seattle||Chicago||Thu, Nov 13 - Sat, Nov 15||Frontier Airlines||$289|
|Philadelphia||Chicago||Fri, Nov 7 - Sat, Nov 8||American Airlines||$227|
|Newark||Chicago||Fri, Nov 14 - Mon, Nov 17||Delta Air Lines||$232|
|Portland||Chicago||Fri, Oct 31 - Sat, Nov 1||Spirit Airlines||$147|
|Atlanta||Chicago||Fri, Dec 12 - Sun, Dec 14||Frontier Airlines||$115|
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.