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Low fares for San Diego (SAN) to Chicago (CHI) Low fares for San Diego to Chicago
Wed 09/27 - Sat 09/30
3 days, 0 stops max
$97
Mon 10/16 - Tue 10/17
1 day, 0 stops max
$97
Tue 11/14 - Tue 12/05
21 days
$129
Wed 12/06 - Tue 12/12
6 days
$119
Thu 01/25 - Thu 02/08
14 days
$121
Wed 02/07 - Thu 02/08
1 day
$121
Tue 10/17 - Tue 10/31
14 days
$119
Wed 09/27 - Tue 10/17
20 days
$119
Tue 10/03 - Tue 10/17
14 days
$119
Wed 10/18 - Tue 10/31
13 days
$119
Sat 09/30 - Tue 10/17
17 days
$119
Fri 09/29 - Tue 10/17
18 days
$124
Cheap flights to Chicago recently found by travelers *
Arriving at the Chicago Airport

Chicago, one of America’s largest cities, has two major airports: O’Hare and Midway. O’Hare is Chicago’s primary airport; however Chicago Midway International Airport is 10 miles closer to the Loop, one of Chicago’s biggest attractions. You can find cheap airfare to either of these locations. If you need wheelchair assistance or other special services, be sure to denote that when booking your flight to Chicago—Traveler’s Aid Chicago is an agency in O’Hare that can assist you with any additional needs. Whether you’re traveling within the U.S. or from abroad, it’s easy to find cheap flights to Chicago whenever you want to visit.

Getting Around Chicago

Your flight to Chicago has arrived, and now you need to get downtown. The quickest and most economical way to reach downtown is the Chicago Transit Authority elevated (L) trains. Limousines, taxis, and airport shuttle buses are always available, but may not be the most cost efficient method of transportation. If your airfare to Chicago includes a car rental, you may want to leave your car at the hotel and use public transportation to avoid the frustrations of hectic traffic and limited parking.

Main attractions In Chicago

Chicago can satisfy your interests, whatever they may be. A trip to the Chicago Cultural Center is a fun way to start your trip. Millennium Park is a popular destination for locals and visitors because it is filled with award-winning art and architecture in a setting the whole family can enjoy. If your flight to Chicago is during the summer, be sure to check out one of the numerous blues and jazz music festivals. The Air and Water Show and the Kite Festival are fun family-friendly events. At sunset, grab a drink at The Ledge at Chicago’s Skydeck, where you can watch Chicago light up at night from the best viewpoint in town.

Shopping, Dining, and Nightlife in Miami

Your flight to Chicago brought you to a shopping and fashion capital that caters to any shopper’s needs. Not only are all the major department stores and chic designer boutiques part of the vibrant retail landscape, but there are many Chicago-based fashion designers with id boutiques. With the money you have saved on your cheap airfare to Chicago, you can indulge in the city’s plentiful shops. Whether you took a flight to Chicago flight for business or pleasure, visitors must go out and enjoy the city’s wide variety of cuisine. Restaurants serve everything from Chicago-style hot dogs to gourmet cuisine, elegant desserts, or pierogies and pizza.

Take a cheap flight to Chicago and enjoy a fun weekend in a town with great nightlife. The Buddha Lounge offers is a great place to dance or just kick back and listen to DJs mixing world, electric, soul, funk, hip-hop, and more. A flight to Chicago is a great way to take a break from a busy schedule at any time during the year.

Flight stats for Chicago - did you know?
  • Chicago is 9 mi from Midway Airport (Chicago, IL).
  • Midway Airport (Chicago, IL)
    • Right now, 10 airlines operate out of Midway Airport.
    • Midway Airport offers nonstop flights to 75 cities.
    • Every week, at least 1,873 domestic flights and 79 international flights depart from Midway Airport.
  • Chicago is 16 mi from O'Hare Intl Airport (Chicago, IL).
  • O'Hare Intl Airport (Chicago, IL)
    • Right now, 81 airlines operate out of O'Hare Intl Airport.
    • O'Hare Intl Airport offers nonstop flights to 212 cities.
    • Every week, at least 22,760 domestic flights and 2,439 international flights depart from O'Hare Intl Airport.

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