• Search over a Million Flights

  • No cancellation fee to change or cancel

Call Now for Unpublished Fare

Destination Banner

Flights From

Chicago to Dallas From
US$ 289.40*
Book Now
Chicago to Las Vegas From
US$ 324.40*
Book Now
Chicago to Los Angeles From
US$ 318.40*
Book Now
Chicago to Denver From
US$ 269.60*
Book Now
Chicago to Miami From
US$ 221.40*
Book Now

Flight Under $199 Deals Insights

Popular Routes

Denver-NYC, Miami-Seattle, NYC-Rome, Las Vagas -Madrid

Popular Routes

Denver-NYC, Miami-Seattle, NYC-Rome, Las Vagas -Madrid

Popular Routes

Denver-NYC, Miami-Seattle, NYC-Rome, Las Vagas -Madrid

Popular Routes

Denver-NYC, Miami-Seattle, NYC-Rome, Las Vagas -Madrid

Save $150 On select flight + hotel packages with promo code: sightsee150 >

Cheap Flights To Chicago (CHI), Illinois

The Mid West’s Capital, Chicago, a hustling metropolis crammed with adrenaline downtown is among the largest cities in the US. Famed for its bold architecture, the city offers several art institutes. You can listen to blues and jazz in the historic avenues or free spirit yourself around the city center.

This third most populous city in the US is also known as the shopper’s paradise, with the craft market at Lincoln Square, the never-ending supply of boutiques on Michigan Avenue, and much more to see. You can book cheap flights to Chicago today with VaccationTravel and unearth amazing cuisines suiting your taste buds perfectly.

Things to do in Chicago

Chicago is a global hub for finance, culture, commerce, industry, and transportation. This extraordinary city has all; theatre, nightlife, diverse cuisine, festivals, events, warm people, and more.

This windy city feels like home and throughout your stay, you’ll experience something fresh. Wander from national forests of the south to the historic river towns in the north, ingesting the assets of this beautiful city. Here is a list of few places to visit before you leave Chicago;

  • Shedd Aquarium- This place is home to more than 1500 species of sea life and features the very popular beluga whales and dolphins.
  • Field Museum of natural history- Witness the Tyrannosaurus skeleton here and millions of specimens, be it an adult or a kid, everyone loves a little science tour.
  • Chicago water tower- This ecstatic limestone structure is home to the gallery of the city exhibiting the work of local artists and photographers.
  • Millennium park- There are modern sculptures in steel to look forward to apart from a lot of open space and greenery. It is the new photo spot for visitors.
  • Navy pier- An ideal destination for a family. It comprises gardens, IMAX theatre, restaurants, Ferris wheel and more.

Chicago offers plenty of things including tours, spectator sports, and other attractions. You are in the right mix of cuisines as well. Contrary to popular belief, Chicago is not restricted to just pizzas and hot dogs, there is so much more on the platter to hog. Prepare your taste buds to savor some of the best authentic American food. Chicago presents local specialties and gourmet dinners; then there is fine Italian beef and Greek gyros, tacos, steaks and so much more. 

You’ll also discover comedy clubs, casinos, craft breweries, sophisticated piano bars, swanky clubs, sultry blues and jazz clubs to consort and feel the rush. This city sure knows how to revel and let the hair down. Here are a few lit up places in the streets of Chicago to be a night owl and burn the floor; 

  • Chicago Magic Lounge
  • Chicago Detours
  • Jazz Showcase
  • Lagunitas Taproom
  • B.L.U.E.S.

The paramount time to visit Chicago is amongst April-May and September-October. Several festivals like the Magnificent Mile, Chicago Blues, etc. are taking place at this time and the weather is stunning as well. Though the lodging rates are little towering, explore the packages available with VaccationTravel for cheap round trip flights to Chicago and hotels to bag the most economical prices.

Airport in Chicago

Chicago has two airports Chicago Midway International Airport and Chicago O’Hare International Airport. Numerous first class, business class and premium economy flights to Chicago are boarded every day by over a million travelers.

Chicago Midway International Airport is situated 10 miles southwest of downtown Chicago. Flights largely imminent from low-cost carriers offer cheapest one-way flight tickets to Chicago with just one terminal bustling frequently. There are taxis, buses, and trains available to and from the airport.  Conveyance around the city is also decent through similar amenities.

Chicago O’Hare International Airport is situated 18 miles northwest of Chicago and is the world’s sixth-busiest airport serving 83 million passengers. There are four terminals and the shuttle service is readily available for travelers constantly. Services like buses, trains, and taxis are offered through the city and around the airport as well. Book cheap business class flight tickets to Chicago with the best price and through world-class carriers via VaccationTravel.

The services presented at both the airports are similar and carry off the concern of uninterested between your flights. The airport offers countless services for travelers to fancy. There are currency exchange booths, luggage facilities, lounges, play areas, a number of shops, plenty of restaurants and bars with diverse other services too.

Hotels in Chicago

The bustling city is popularly known for its business and culture all around the world. Facilitate all your needs of a comfortable stay, attractions within reach, and good restaurants around at decent rates.

Book a discounted flight to Chicago today with hotels and survey other discounts available at VaccationTravel. We provide a hassle-free booking experience offering a suitable place for your stay.

Here are a few hotels that can be considered when you reach Chicago:

  • Palmer House A Hilton Hotel
  • Travelodge by Wyndham Downtown Chicago
  • The Blackstone, Autograph Collection
  • JW Marriott Chicago
  • Silversmith Hotel Chicago Downtown

Traveling Tips for Chicago

Avoid flying in and out of O’Hare international airport as the number of travelers is high and delay is certain. Explore the wide variety of cuisines instead of eating pizza and you will be astonished by the versatility of this city. Chicago has a lot more to explore so don’t restrict yourself to downtown, go ahead and make the most out of it. 

Check-out the museums for the display of the art of all kinds. Book best airline deals on first class flight to Chicago with VaccationTravel and save your money. Spend that amount on the Broadway shows and other excursions creating memories worth remembering.

Airlines Which Fly to Chicago

Inexpensive deals on round trip flight to Chicago on hand with the following carriers;

  • American Airlines
  • Frontier
  • Spirit
  • United
  • Virgin America
  • JetBlue
  • Delta
  • Aero Mexico 
  • Copa Airlines 
  • Caribbean Airlines  
  • Air Canada
  • British Airways 
  • Lufthansa 
  • Emirates


We believe in Customer Satisfaction, not just the Business..! (Know what customers say about us)