Exclusive Cheap Flight Travel Deals for Chicago

Vacay Flights guarantees you the best deals and offers on your flight bookings for Chicago that will let you save big.  The flight booking process with us is quick and easy that promises a hassle-free journey. We make sure that you get notified every time the price of Chicago flight tickets drop. Also, if you have to take an immediate emergency flight, you can avail deals and discounts on last minute flights to Chicago from any US cities in no time.

Which US cities have flights to Chicago?

Chicago enjoys good flight connectivity to US cities by airways. Following are some of the top US cities with flights to Chicago:

  • Atlanta to Chicago
  • New york to Chicago
  • Los Angeles to Chicago
  • Washington DC to Chicago
  • Philadelphia to Chicago
  • Dallas to Chicago
  • Miami to Chicago
  • Boston to Chicago
  • Detroit to Chicago
  • Houston to Chicago
  • Orlando to Chicago
  • Minneapolis to Chicago
  • San Diego to Chicago

Airports Near Chicago For Cheap Flights

Chicago has four airports nearby with cheaper air tickets. If you are flexible, you might save big on flight tickets to these nearby airports to Chicago.

  • Chicago Midway Airport: 16 miles from Chicago O’Hare International Airport
  • Chicago Dupage County Airport: 18 miles from Chicago O’Hare International Airport
  • Chicago Rockford Airport: 71 miles from Chicago O’Hare International Airport
  • Milwaukee General Mitchell Airport: 67 miles from Chicago O’Hare International Airport
Which are the major airports in Chicago

While there are many domestic and international airports in Chicago providing connectivity to different regions, Chicago O’Hare International Airport happens to be the largest and main airport of all. The other important airports of Chicago are as follows:

    • Chicago O’Hare International Airport
      0000 W O’Hare Ave, Chicago,
      IL 60666, United States
Chicago Midway International Airport
5700 S Cicero Ave, Chicago,
IL 60638, United States
  • Chicago Rockford International Airport
    2 Airport Cir, Rockford,
    IL 61109, United States
  • Chicago Dupage County Airport
    2700 International Dr, West Chicago,
    IL 60185, United States

Tips on how to get cheap flight tickets to Chicago
  • Sign-up for flight alerts to get notified when the prices of Chicago flight tickets drop.
  • Book your Chicago flight tickets as early as one or two months to avail best deals.
  • If your schedule permits, try flying to Chicago on days like Tuesday, Wednesday or Saturday as it lands you a cheaper fare.
  • Travel during the summer months i.e., January to March that are considered to be the best months to avoid the higher-priced tickets to Chicago.
Which is the cheapest month to fly to Chicago?

January to March: the summer months in Chicago see prices dipping to their lowest levels.

Which are the three popular airlines flying to Chicago?

Chicago is connected by a number of airlines that not only offer regular flights with cheaper air fare as well. Some of the popular airlines with flights to Chicago are:

  • American Airlines
  • Alaska Airlines
  • Southwest Airlines


Which is the best month to visit Chicago

April to May and between September and October are the best months to visit Chicago. During these months, the temperature is pleasant and a variety of festivals and other activities can be enjoyed.
Areas to book hotels in Chicago
Near airport:

  • North Cumberland Avenue
  • Touhy Avenue
  • E Lake St. Addison Township
  • North Milwaukee Avenue
  • South Milwaukee Avenue
  • Pearl Street, Rosemont
  • North River Road, Rosemont
  • North Mannheim Road, Rosemont
  • W Bryn Mawr Ave, Rosemont
  • West Higgins Road, Rosemont
  • West Bryn Mawr Avenue
  • West Algonquin Road
  • Lee Street, Des Plaines
  • East Touhy Ave, Des Plaines
  • North River Road, Schiller Park

Near Attractions in Chicago

  • Chicago Loop/Downtown

City Centre:

  • Downtown

Low-Cost Areas

  • Ohio Street
  • North LaSalle Street
  • Touhy Avenue
  • W Kinzie Street


What are the top things to know about Chicago?

Chicago leaves you spoiled for choice with its amazing sights and experiences. Here’s what you must know about Chicago.

  • Chicago loves to provide excellent taste of food to locals and tourists coming from across the world. For this reason, the city hosts the largest outdoor food festival: ‘The Taste of Chicago’ for five consecutive days in July.
  • The city is home to the only river in the world that flows backwards. The reverse flowing of the river was acknowledged as a great engineering achievement.
  • It is in Chicago where Twinkie was launched in 1930. The original Twinkie was filled with banana cream, but later during WWII it was replaced with vanilla cream when bananas became scarce. So those with a sweet tooth, make sure you try out the delicious Twinkies when in Chicago.
  • The first blood bank in the US was established in Chicago in 1937.
  • The Ferris Wheel was invented in this city in 1893. An amusement ride on the Ferris Wheel when visiting Chicago would be so much fun. Isn’t it?


What are the top things to see & do in Chicago?

Booked your flight ticket to Chicago? Now learn about the top attractions in Chicago for your best sightseeing experience.

  1. Garfield Park Conservatory
  2. Chicago Riverwalk
  3. Millenium Park
  4. Willis Tower Skydeck
  5. Lincoln Park Zoo
  6. Field Museum of Natural History
  7. Lost Lake
  8. Chicago Pizza Tour
  9. WhirlyBall
  10. Shedd Aquarium
  11. Stroll/Cycling on the Bloomingdale Trail
  12. Attend a Music Festival
  13. Shopping at Maxwell Street Market
What are the top tourist attractions near Chicago?

The neighbouring destinations in Chicago also have a lot to offer to a traveller. If you have got a one way ticket to Chicago, the amazing destinations around it are a must visit.

  • Indianapolis, Indiana: 183 miles from Chicago
  • Milwaukee, Wisconsin: 92 miles from Chicago
  • Madison, Wisconsin: 147 miles from Chicago
  • Toledo, Ohio: 244 miles from Chicago
  • Detroit, Michigan: 282 miles from Chicago
  • Cincinnati, Ohio: 295 miles from Chicago
Which are the popular festivals of Chicago?

Chicago  hosts some incredible festivals in the US. Make sure to book your flights to Chicago, Illinois  to attend some of the  best festivals in the city.

  • Randolph Street Market Festival (February, April to July, September to December)
  • Chicago Beer Festival (March)
  • Chicago Flower & Garden Show (March)
  • Eataly’s Spring Fest (March)
  • Chicago Latino Film Festival (April)
  • Chicago Humanities Festival’s Spring Fest (April-May)
  • Manifest Urban Arts Festival (May)
  • Chicago Zine Fest (May)
  • Chicago Kids and Kites Festival (May)
  • Chicago Wine Fest (May)
  • Chicago House Music Festival (May)
  • Chicago Gospel Music Festival (May)
  • Chicago in Tune Music Festival (May)
  • Puerto Rican Festival Virtual for (May)
  • Hyde Park Summer Fest (June)
  • Craft Beer Festival (June)
  • Logan Square Arts Fest (June)
  • Chicago Blues Festival (June)
  • Grant Park Music Festival (June-August)
  • Chicago Margarita Festival (July)
  • Taste Of Lincoln Avenue (July)
  • Taste of Chicago (July)
  • African/Caribbean International Festival Of Life (July)
  • Pitchfork Music Festival (July)
  • Irish American Heritage Festival (July)
  • Chosen Few DJs Picnic & Music Festival (July)
  • Ukrainian Days Festival (August)
  • Taste Of Greektown (August)
  • Square Roots Music Festival (August)
  • Wells Street Art Festival (August)
  • Chicago Jazz Festival (August)
  • Sangria Festival (August)
  • Chicago Women’s Funny Festival (August)
  • Ginza Festival (August)
  • Lollapalooza (July to August)
  • South Shore Summer Festival (August)
  • North Coast Music Festival (September)
  • World Music Festival Chicago (September)
  • Lakeview East Festival of the Arts (September)
  • Millennium Art Festival (September)
  • Chicago International Latino Theater Festival (September/October)
  • Magnificent Mile Lights Festival (November)
  • Winter Wonderfest (Dec- Jan)
  • Chicago Sketch Comedy Festival (January)
  • Fillet of Solo Festival (January)
  • Chicago Ale Fest (January)
  • Rhinoceros Theater Festival (January)
  • Chicago Chinese New Year Celebration (January-February)
  • University of Chicago Folk Festival (February)
  • Chicago Flamenco Festival (February-March)
Things to know before you book your flights to Chicago

In order to make your experience of travelling to Chicago hassle-free and convenient, get some information on its local transport, language and currency.
Currency: The US Dollar (USD) is used in Chicago and all of the USA.
Language: English is the primary language used for communication in  Chicago.
Local Transport: Chicago is served by local trains, buses, shuttles, streetcars, taxis (road and water) , and ride-sharing services.