Cheap Flights to Chicago from $27

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How Much Does it Cost To Fly To Chicago?

The cheapest prices found with in the last 7 days for return flights were $53 and $27 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
BWIChicagoApril 10 to April 17$68
BWIChicagoApril 16 to April 23$102
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
DCAChicagoMarch 24 to April 9$372
IADChicagoMarch 24 to March 27$461
*Prices include taxes and fees

Chicago ORD Flight Information

Traveling to
Chicago ORD
Lowest Price
$53
Number of Airlines Serving
12
Airlines Serving
Spirit Airlines, Frontier Airlines
Number of Daily Flights
44
Airlines with Direct Flights
American Airlines, Qatar Airways, Alaska Airlines, JAL, Cathay Pacific, Emirates, Royal Jordanian, SAS, ANA, Air New Zealand, United Airlines, British Airways

Find The Perfect Hotel For After Your Flight

Amazing Chicago Accommodation Deals

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
The price is $58 per night from Mar 31 to Apr 1
$58
per night
Mar 31 - Apr 1
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.6/10 Good! (1,005 reviews)
"Good choice for the price. The location is surrounded by lots of other hotels, and is close to downtown attractions."

Reviewed on Mar 16, 2024

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $80 per night from Mar 20 to Mar 21
$80
per night
Mar 20 - Mar 21
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.2/10 (1,567 reviews)
"Like the place 😃"

Reviewed on Mar 16, 2024

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $60 per night from Mar 26 to Mar 27
$60
per night
Mar 26 - Mar 27
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,146 reviews)
"Generally speaking, my expectations were lower than, what I really experienced at the motel. Best place for the price!"

Reviewed on Mar 17, 2024

Motel 6 Elk Grove Village, IL - O'Hare
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Ohio House Motel

Ohio House Motel

2.5 out of 5
600 N La Salle Drive, Chicago, IL
The price is $82 per night from Mar 21 to Mar 22
$82
per night
Mar 21 - Mar 22
Stay at this motel in Chicago. Enjoy free WiFi, onsite parking, and a 24-hour front desk. Our guests praise the helpful staff and the convenient parking in our ...
8.8/10 Excellent! (1,003 reviews)
"The rooms were nice and clean but parking was inconvenient. And to put down a deposit is more than the rate of the room."

Reviewed on Mar 11, 2024

Ohio House Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Our Top Chicago with Airport Shuttles

Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

2.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
The price is $72 per night from Mar 20 to Mar 21
$72
per night
Mar 20 - Mar 21
Stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,003 reviews)
Clean, on the highway, large room
"Just got here😃"

Reviewed on Mar 16, 2024

Super 8 by Wyndham Chicago O'Hare Airport
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 East Grand Avenue, Bensenville, IL
The price is $76 per night from Mar 31 to Apr 1
$76
per night
Mar 31 - Apr 1
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions ...
6.4/10 (1,001 reviews)
"."

Reviewed on Mar 11, 2024

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

2.5 out of 5
3939 N Mannheim Rd, Schiller Park, IL
The price is $89 per night from Mar 24 to Mar 25
$89
per night
Mar 24 - Mar 25
Stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,249 reviews)
"I would go back."

Reviewed on Mar 17, 2024

Hampton Inn Chicago-O'Hare International Airport
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Holiday Inn Chicago O'Hare Area, an IHG Hotel

Holiday Inn Chicago O'Hare Area, an IHG Hotel

3 out of 5
5615 North Cumberland Avenue, Chicago, IL
The price is $94 per night from Apr 1 to Apr 2
$94
per night
Apr 1 - Apr 2
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast. Our guests praise the breakfast and the helpful staff in ...
7.4/10 Good! (1,000 reviews)
"Does everything it’s supposed to do."

Reviewed on Mar 10, 2024

Holiday Inn Chicago O'Hare Area, an IHG Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Chicago

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
401 N Wabash Ave, Chicago, IL
The price is $348 per night from Mar 24 to Mar 25
$348
per night
Mar 24 - Mar 25
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our ...
9.2/10 Wonderful! (1,111 reviews)
"Excellent location, amazing hotel."

Reviewed on Mar 17, 2024

Trump International Hotel & Tower Chicago
The Langham, Chicago

The Langham, Chicago

5 out of 5
330 North Wabash Avenue, Chicago, IL
The price is $370 per night from Apr 14 to Apr 15
$370
per night
Apr 14 - Apr 15
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our ...
9.6/10 Exceptional! (1,003 reviews)
"Everything was awesome."

Reviewed on Mar 17, 2024

The Langham, Chicago
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
108 East Superior Street, Chicago, IL
The price is $450 per night from Mar 24 to Mar 25
$450
per night
Mar 24 - Mar 25
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a full-service spa. Our guests praise the helpful staff and the property condition ...
9.6/10 Exceptional! (1,003 reviews)
Amazing Hotel!
"Amazing! Friendly staff, beautiful room, and a spa on site!"

Reviewed on Mar 17, 2024

The Peninsula Chicago
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The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
521 North Rush Street, Chicago, IL
The price is $209 per night from Mar 22 to Mar 23
$209
per night
Mar 22 - Mar 23
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,001 reviews)
"very nice"

Reviewed on Mar 8, 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Great for families

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive, Chicago, IL
The price is $136 per night from Mar 31 to Apr 1
$136
per night
Mar 31 - Apr 1
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, WiFi, and room service. Our guests praise the breakfast and the helpful staff in ...
8.2/10 Very Good! (2,355 reviews)

Families like: Indoor pools, close to beach, bicycle rentals nearby, extra beds/cribs

Travelers say...
"The breakfast is amazing!!!"

Reviewed on Mar 16, 2024

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel
Great for families

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
The price is $139 per night from Mar 31 to Apr 1
$139
per night
Mar 31 - Apr 1
Stay at this 4-star spa hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour health club. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,126 reviews)

Families like: Indoor pools, close to beach, bicycle rentals, extra beds/cribs

Travelers say...
"Very busy in Chicago, St Patrick’s day!"

Reviewed on Mar 17, 2024

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North
Great for families

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is $124 per night from Mar 31 to Apr 1
$124
per night
Mar 31 - Apr 1
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
7.8/10 Good! (2,117 reviews)

Families like: Indoor pools, close to beach, bicycle rentals nearby, extra beds/cribs

Travelers say...
"There were some parts of the room near door handles that weren't clean."

Reviewed on Mar 16, 2024

Embassy Suites by Hilton Chicago Downtown River North
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Hyatt Regency Chicago
Great for families

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
The price is $161 per night from Mar 31 to Apr 1
$161
per night
Mar 31 - Apr 1
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the breakfast and the restaurant ...
8.8/10 Excellent! (3,487 reviews)

Families like: Close to beach, bicycle rentals nearby, extra beds/cribs, laundry

Travelers say...
"Very nice"

Reviewed on Mar 18, 2024

Hyatt Regency Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best Chicago Flight and Hotel Packages

Chicago flight + hotel packages - economy flights

Level Chicago – Old Town
Trump International Hotel & Tower Chicago
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Don't see what you're looking for?
See all available trips from WAS-All Airports to Chicago
View all trips
Prices and availability subject to change. Additional terms may apply.

Need a Car For After Your Flight?

Frequently asked questions

Which airlines fly to Chicago?
When it comes to airlines that offer flights to Chicago, you’re flush with choice. There are 20 companies that service this major city. Choose your favorite seat on one of these top carriers:

  • United Airlines
  • American Airlines
  • Southwest Airlines

What airport is best to fly into Chicago?
There are two airports servicing Chicago. If you fly into O’Hare Intl. Airport (ORD), you’ll be 16 mi from the city center. The second option is Chicago Airport, roughly 9 mi from all the action of the downtown area.
Where to stay in Chicago
Researched Chicago, planned your vacation outfits but haven’t yet locked in a place to stay? Travelocity can help. Select from 5,030 centrally located properties and start packing your bags!It’s time for your vacation! Why not treat yourself to luxury? If you’ve been dreaming of first-class service and soft, silky sheets, book the Palmer House a Hilton Hotel or the Silversmith Hotel Chicago Downtown. That being said, you wouldn’t go on vacation to stay in your room all week. If you’ve been looking for a more wallet-friendly option, consider the Hi Chicago or the Travelodge by Wyndham Downtown Chicago.Traveling is about absorbing those extraordinary sights. If McCormick Place is number one on your itinerary, you may want to stay a stone’s throw away. The Hyatt Regency McCormick Place is 0.1 mi away, while the Marriott Marquis Chicago is 0.2 mi away.
Places to visit in Chicago
With so many remarkable attractions in Chicago, you might just have to tell your boss you need another week off. Start off with Art Institute of Chicago, and Millennium Park. You’d also be mad not to explore Skydeck Ledge, and Willis Tower.Ardent sightseers will want to visit Chicago Cultural Center, and Buckingham Fountain. After more things to see in this buzzing city? Merchandise Mart, and Wrigley Building should keep you occupied.Attend a play at Chicago Theatre and see the plot thicken! Seeking some more options? Many of the most popular attractions are located in Chicago Riverwalk area. And that’s not all. Stop and look at Water Tower Place. You’ll be able to see this impressive local skyscraper from different locations around town.
How to get through airport security fast when traveling to Chicago
Make your trip to Chicago a little easier by following these helpful tips and pointers:

  • Make sure you know the location of your travel ID and boarding pass. You don’t want to hold up the line when you’re asked to present them.
  • It’s helpful to know that belts with metal buckles can set off the body scanner’s alarms. If you have one on, you may be told to remove it before moving on.
  • Digital cameras, laptops and other electronic devices must be placed in separate tubs to be X-rayed.
  • When it comes to flying with liquids or gels, every passenger is allowed a quart-sized clear resealable bag to transport containers no bigger than 3.4 ounces (100 milliliters).
  • Undo your shoelaces as you approach the body scanner. Depending on the style of shoes you’ve got on, security may tell you to remove them.
  • Pack any multi-tools or other pointy metal items inside your checked luggage. Security personnel don’t permit these on the plane.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Flights To Chicago

Each time you visit Chi-Town, you’ll fall in love anew. Even if you’ve stood in front of the famous metallic bean and stood along the Navy Pier, you won’t be left wanting for original ways to spend your time. As Mark Twain posited, “She is novelty, for she is never the same Chicago you saw when you passed through the last time.” The modern city on the shores of Lake Michigan is always evolving and will never fail to enchant you. Between the exciting sports culture and buildings that hearken back to a time when Frank Sinatra and Al Capone ran the scene, Chicago always impresses.

Flights to Chicago depart from tons of destinations; just sit back, start dreaming of deep-dish pizza, and before you know it you’ll be touching down in the Windy City. Book your airfare on Travelocity today, and you’ll save enough cash to afford all the famous frankfurters you want.

Transportation from Chicago Airports

Chicago flights land at one of the two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). Getting to downtown Chicago from ORD is a breeze when you take the Blue line train, which is part of the Chicago Transit Authority train system. From MDW, jump on the Orange line train.

If you’re not staying downtown, buses are available to most parts of the city from both airports. When a private ride is more your style, hail a taxi outside the baggage claim area. Many hotels also have shuttle buses that will take you to and from the airport. But if independence is more your style, there are many rental car companies located within the airport if you need your own wheels; book your ride when you purchase your airfare to Chicago and your vacation is set.

Hotels Near ORD and MDW

A savvy traveler such as yourself is sure to purchase one of our top flight deals to Chicago. Not only will you travel on one of the most affordable and convenient flights, but you’re wise enough to book a Chicago hotel befitting of your fine taste:

  • The Palmer House Hilton: This hotel bills itself as hip and historic, and one step inside the lobby lets you know the description is spot on. Opulent ceilings and marble accents remind you of an era when dinner was always a formal affair, while the rooms are adorned in bright furniture and clean modern lines.
  • Wyndham Grand Chicago Riverfront: From the cocktails served fireside at Hoyt’s Patio to in-room massages, this downtown hotel is designed to pamper. Get a room with a view and overlook the Windy City from the moment you wake up, and let the concierge help you book excursions to Chicago attractions.
  • Hyatt Regency Chicago: This four-diamond hotel is connected to the Illinois Center downtown, right in the heart of the city. You’ll be just a short and leisurely walk from the Magnificent Mile and Grant Park.
  • Congress Plaza Hotel: Legendary hotels are just your style, so this Grant Park hotel has your name on it. Enjoy a view of Lake Michigan from your room, and revel in the property’s storied history, which dates back to 1893.

Things to Do in Chicago

The Windy City is known for its pizza and beloved sports teams, but the Midwest powerhouse packs a cultural punch and can impress even seasoned world travelers. Begin your exploration with an investigation of Millennium Park, and then get a taste of Chi-Town’s creative offerings at the Art Institute of Chicago. From the observation deck of the Willis Tower, you can spot your favorite attractions and plot your route of the city. Like the savvy tourist you are, you booked cheap plane tickets to Chicago. Go ahead, buy entrance to the Lincoln Park Conservatory and Brookfield Zoo.

Use Travelocity to search through the flight options to the Windy City. Once you find one of the cheapest flights to Chicago and buy your tickets, there is nothing left to do but start dreaming of mozzarella and pack your bags. Chi-Town is waiting to welcome you with open arms and delight you with its Midwest charms.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.