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Top Flight Deals Last Updated September 27, 2022 4:10 AM

Handpicked Chicago One Way Flight Deals

  • ATLAtlanta October 19, 2022
  • CHI Chicago
  • $47.77*
  • PHLPhiladelphia October 05, 2022
  • CHI Chicago
  • $67.79*
  • ORLOrlando October 05, 2022
  • CHI Chicago
  • $77.79*
  • MSYNew Orleans October 04, 2022
  • CHI Chicago
  • $103.37*

Handpicked Chicago Round Trip Flight Deals

  • MBLManistee December 01, 2022
  • CHI Chicago December 02, 2022
  • $158.50*
  • NYCNew York October 22, 2022
  • CHI Chicago October 26, 2022
  • $173.20*
  • HOUHouston October 27, 2022
  • CHI Chicago October 31, 2022
  • $188.96*
  • BUFBuffalo December 13, 2022
  • CHI Chicago December 31, 2022
  • $195.96*
  • ONTOntario October 01, 2022
  • CHI Chicago October 05, 2022
  • $200.17*
  • DECDecatur October 10, 2022
  • CHI Chicago November 20, 2022
  • $208.80*
  • COSColorado Springs March 15, 2023
  • CHI Chicago March 18, 2023
  • $209.96*
  • ALBAlbany September 30, 2022
  • CHI Chicago October 03, 2022
  • $210.79*
  • CVGCincinnati October 10, 2022
  • CHI Chicago October 11, 2022
  • $211.97*
  • BURBurbank October 25, 2022
  • CHI Chicago October 28, 2022
  • $212.77*

Incredibly low Chicago Airline Ticket Reservations on TravelReImagine!

Chicago, the windy city is located on Lake Michigan in the state of Illinois. It is famous for its skyline punctuated by tall skyscrapers with likes of erstwhile tallest building in the world Sears Tower, now called Willis Tower. It is known for its vibrant arts scene, cultural attractions, amazing shopping, and bold architecture of 20th century. The Navy Pier, Michigan Avenue and the Magnificent Mile will be interesting destinations to spend time and keep you busy for the whole day. Also, beautiful beaches on the shores of lake Michigan are too good for sun and water lovers. WithTravelReImagines’ big discounts on Chicago flights you can visit Chicago while saving massive on flights to Chicago.

Best time to visit Chicago

Summer months from June through August are the best time to visit Chicago with clear outdoors. However, summer is the peak season when the highest number of tourists visits the city which tends to make the flights and hotels costlier. Therefore, travellers are advised to book their flights to Chicago well in advance.

How to arrive at Chicago?

O'Hare International Airport (ORD), one of the largest airports in United States is the main entrance to the city. O’Hare International Airport is served by most of the major national and international airlines such as Delta Airlines, American Airlines, British Airways, Cathay Pacific and United Airlines, with connections to major cities like Atlanta, Los Angeles, Washington DC, Seattle, New York, Hong kong and London, on a daily basis.

3 Best Places to Visit in Chicago

The Art Institute of Chicago

It is a world class museum sprawling over 400,000 square feet. The museum displays innumerable and diverse collection of paintings, prints, photography, architectural drawings, sculptures, decorative arts, textiles and much more.

Millennium Park

This is located in Grant Park, downtown Chicago, a must visit destination for visitors. Cloud Gate, a 110-ton sculpture is a centerpiece attraction which has a polished stainless-steel surface reflecting the surroundings. Another top attraction in this park is the Crown Fountain.

Navy Pier

This spot offers gardens, attractions, shops, restaurants, concert venues, and parks for visitors to enjoy and spend time. Also, you can see 150 ft Ferris wheel, watch a film at the 3D Imax Theater, watch actors perform the classics at the Chicago Shakespeare Theater, or visit Crystal indoor botanical garden.

3 Best Things to do in Chicago

Wine and dine to your heart out at Chicago

Culinary scene along with the exciting night life of Chicago makes the city full of fun for the visitors, from fine dining restaurants, cafes, street trucks, nightclubs to bars at your disposal. The city offers one of the best restaurants including Superdawg Drive-In, Smoque BBQ, Parachute, Honey Butter Fried Chicken, Paulie Gee's Logan Square, Pequod's Pizza. In addition to this, Uvae Kitchen and Wine Bar, Lost Larson, Angelo's Wine Bar, Volo Restaurant Wine Bar, Eno Wine Bar and Figo Wine are some of the best places to drink while in the city.

Experience amazing one-of-a-kind Festivals

Chicago’s festivals and unique events attract visitors from all over the globe, offering a plethora of parades and celebrations. Chicago festival in August, Chicago Gospel Music Festival, Chicago Jazz Festival, Taste of Chicago and World Music Festival Chicago,are some of the best festivals to enjoy in Chicago.

Enjoy the bird’s eye view of Chicago from the SkyDeck

This tour is a must when you are in Chicago. The SkyDeck is an observatory on the top of 110 storied Willis Tower with glass floor. The view from here is incredible, you can see up to 40 to 50 miles and a bird's eye view of Chicago's impressive and bold architecture.

Best places to do shopping in Chicago

Some of the best places to shop in Chicago are the Woodfield Mall, Andersonville, River North, State Street in Downtown, Fashion Outlets of Chicago, Water Tower Place, Lincoln Square/Ravenswood, Oak Street and the Gold Coast.

Tips to save more on Chicago Flights

TravelReImagine’s affordable Chicago flight deals, you can now book discount Chicago flights and take a vacation to Chicago without splurging much on Chicago airfares. We offer exclusive Chicago airline tickets with which you can have incredible savings on flights to Chicago. However, incorporating the following tried and tested tips can ensure some extra savings on Chicago flights tickets.

  • Check and compare Chicago flight prices with all airlines offering flights to Chicago to grab the best deals on Chicago flights.
  • Traveling on Tuesday, Wednesday and Saturday can ensure the cheapest and most guaranteed way to reduce your expenses on Chicago airline tickets.
  • Code sharing can help you save more on Chicago airfare.
  • Consider traveling to Chicago on winters from January through February as the prices of Chicago flights usually plunge during the off-season.
  • Flying to an alternative nearby airport rather than the busiest and the most popular one would surely save you a lot on your flights to Chicago.
  • Be informed about every update about the rise and fall of the prices of plane tickets to Chicago by signing up our newsletters.
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*
Fares are Round Trip. Fuel surcharges, our service fees & taxes are all included in the fares. Fares displayed are subjected to availability and may change without notice and cannot be guaranteed at the time of booking. Please check all bookings Terms & Conditions.
**
Fares are Round Trip. Fares include all fuel surcharges, our service fees & taxes. Fares displayed are based on historical data and may change without notice and cannot be guaranteed at the time of booking. To get the lowest fares, an advance purchase of up to 21 days may be required.
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Apply Promo Code – 15OFF & Save up to $15.00**. Applicable - $5 per passenger, maximum – 3 passengers. Promo code is applicable on Domestic & International flights. Book by September 30, 2022.
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