Cheap Flights to Chicago from $29
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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 $49 and $29 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply
LGA
LaGuardia
ORD
O'Hare Intl.
$66 Roundtrip, found 2 hours ago
$66
Roundtrip
found 2 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | Chicago | December 9 to December 16 | $49 |
| ATL | Chicago | December 9 to December 13 | $61 |
| ATL | Chicago | October 2 to October 5 | $97 |
| ATL | Rockford | November 15 to November 15 | $139 |
| LAX | Chicago | October 2 to October 4 | $153 |
| LGA | Rockford | December 6 to December 8 | $158 |
| LAX | Chicago | October 23 to October 27 | $169 |
| DFW | Rockford | December 6 to December 12 | $177 |
| LAX | Rockford | October 22 to October 25 | $201 |
| HKG | Chicago | October 26 to November 29 | $854 |
| PEK | Chicago | October 25 to November 7 | $918 |
| CAN | Chicago | November 20 to November 28 | $949 |
| PVG | Chicago | November 1 to November 17 | $975 |
| XIY | Chicago | November 3 to November 21 | $1,346 |
| HKG | Chicago | September 29 to October 6 | $2,622 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | September 27 to October 1 | $120 |
| ATL | Chicago | September 27 to October 1 | $132 |
| DFW | Chicago | September 27 to October 9 | $151 |
| DFW | Chicago | September 26 to October 4 | $152 |
| LGA | Chicago | September 27 to October 4 | $156 |
| EWR | Chicago | September 27 to September 27 | $156 |
| LAX | Chicago | September 28 to October 4 | $170 |
| LAX | Chicago | September 28 to October 2 | $178 |
| HKG | Chicago | September 26 to September 28 | $855 |
| HKG | Chicago | September 27 to October 14 | $1,010 |
| PEK | Chicago | September 26 to October 19 | $1,172 |
| CAN | Chicago | September 28 to October 7 | $1,236 |
| PVG | Chicago | September 27 to October 5 | $1,276 |
Chicago Flight Information
Traveling to | Chicago |
|---|---|
Lowest Price | $49 |
Number of Airlines Serving | |
Airlines Serving | Spirit Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Chicago Accommodation Deals
Freehand Chicago
19 East Ohio Street, Chicago, IL
$132 nightly
The price is $156 total per night from Sep 23 to Sep 24
$156 total
Sep 23 - Sep 24
Total with taxes and fees
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. ...
7.8/10 Good! (2,341 reviews)
"I loved the character and asthetic of the interior. It was classy, some areas have seen some heavy traffic but it builds the character of the place. I had a shared room with 3 others mostly just kept to ourselves other than a hello or good morning. Staff were very helpful if i had any questions. ..."
Reviewed on Sep 18, 2025
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
$105 nightly
The price is $124 total per night from Sep 22 to Sep 23
$124 total
Sep 22 - Sep 23
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.2/10 Good! (2,352 reviews)
"The location was honestly perfect! It was not far from the train station either coming from out of town. The train was my go-to transportation to get around. My room had a view of the Willis tower which was pretty cool. It’s an older building and nothing fancy, it was simple and had everything I ..."
Reviewed on Sep 18, 2025
Motel 6 Elk Grove Village, IL - O'Hare
2881 Touhy Ave, Elk Grove Village, IL
$55 nightly
The price is $62 total per night from Sep 30 to Oct 1
$62 total
Sep 30 - Oct 1
Total with taxes and fees
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 ...
7.8/10 Good! (1,627 reviews)
"Clean room. Friendly desk staff. Minimalist or budget savvy traveler at O’Hare- book here."
Reviewed on Sep 15, 2025
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Ohio House Motel
600 N La Salle Drive, Chicago, IL
$128 nightly
The price is $150 total per night from Sep 22 to Sep 23
$150 total
Sep 22 - Sep 23
Total with taxes and fees
Stay at this 3-star motel in Chicago. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff and the convenient ...
8.8/10 Excellent! (1,010 reviews)
"Great location & clean rooms. A little noisy"
Reviewed on Sep 16, 2025
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
2951 Touhy Ave, Elk Grove Village, IL
$78 nightly
The price is $88 total per night from Sep 24 to Sep 25
$88 total
Sep 24 - Sep 25
Total with taxes and fees
Stay at this 3.5-star business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7.6/10 Good! (1,431 reviews)
"Good place for the price and close to airport with shuttle service there."
Reviewed on Sep 19, 2025
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
777 E Grand Avenue, Bensenville, IL
$91 nightly
The price is $101 total per night from Sep 22 to Sep 23
$101 total
Sep 22 - Sep 23
Total with taxes and fees
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
7/10 Good! (1,066 reviews)
"Good value. Particularly nice breakfast buffet."
Reviewed on Sep 15, 2025
Hampton Inn Chicago-O'Hare International Airport
3939 N Mannheim Rd, Schiller Park, IL
$115 nightly
The price is $131 total per night from Oct 5 to Oct 6
$131 total
Oct 5 - Oct 6
Total with taxes and fees
Book a 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 ...
9/10 Wonderful! (2,038 reviews)
"Staff was pleasant and the free breakfast was stocked even after the 10am close. It was appreciated. The room was clean enough. The pillows are child-sized, a little annoying for someone who likes to sleep sitting up."
Reviewed on Sep 12, 2025
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Holiday Inn Chicago O'Hare Area by IHG
5615 North Cumberland Avenue, Chicago, IL
$105 nightly
The price is $123 total per night from Oct 5 to Oct 6
$123 total
Oct 5 - Oct 6
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.8/10 Good! (1,006 reviews)
"This is a tired property. Fri didn’t fit in the cabinet, closet doors didn’t close"
Reviewed on Sep 13, 2025
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
401 N Wabash Ave, Chicago, IL
$461 nightly
The price is $541 total per night from Oct 5 to Oct 6
$541 total
Oct 5 - Oct 6
Total with taxes and fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (1,723 reviews)
6 stars
"First time in a Trump property and could not have had a better experience. Everything was perfect! Choose a lakeview room. So worth it!"
Reviewed on Sep 18, 2025
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
$608 nightly
The price is $713 total per night from Oct 5 to Oct 6
$713 total
Oct 5 - Oct 6
Total with taxes and fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,005 reviews)
"The room, staff, facillities, were all above excellent. Keep it up and we will be back."
Reviewed on Sep 12, 2025
The Peninsula Chicago
108 East Superior Street, Chicago, IL
$650 nightly
The price is $763 total per night from Sep 28 to Sep 29
$763 total
Sep 28 - Sep 29
Total with taxes and fees
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9.6/10 Exceptional! (1,006 reviews)
Wonderful experience
"Fabulous luxury hotel! Loved the location. Great vibe enhanced by the cool contemporary art hung throughout the hotel. Room was awesome. Shanghai Terrace was extraordinary for dinner. Hotel brunch was great. Will stay there again."
Reviewed on Sep 16, 2025
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The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
521 North Rush Street, Chicago, IL
$458 nightly
The price is $537 total per night from Oct 19 to Oct 20
$537 total
Oct 19 - Oct 20
Total with taxes and fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our ...
9.4/10 Exceptional! (1,002 reviews)
"Odd layout. Street noise was terrible w racing cars and motor cycles all night."
Reviewed on Sep 13, 2025
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
511 North Columbus Drive, Chicago, IL
$224 nightly
The price is $263 total per night from Sep 22 to Sep 23
$263 total
Sep 22 - Sep 23
Total with taxes and fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,719 reviews)
"The overall experience was a great. Except when I had some setbacks at the airport I had to arrive a day after my husband and kids. The guy at the front desk would not allow them to get the reservation because I was not there. It was a little stressful because it was 1100 at night and the guys said ..."
Reviewed on Sep 15, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
$271 nightly
The price is $313 total per night from Oct 2 to Oct 3
$313 total
Oct 2 - Oct 3
Total with taxes and fees
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,963 reviews)
"Older property rooms need to be upgraded"
Reviewed on Sep 15, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
$185 nightly
The price is $217 total per night from Sep 22 to Sep 23
$217 total
Sep 22 - Sep 23
Total with taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,952 reviews)
"Liked convenient location. Nearby transportation facility. Very nice place to stay!"
Reviewed on Sep 19, 2025
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Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
$319 nightly
The price is $374 total per night from Oct 22 to Oct 23
$374 total
Oct 22 - Oct 23
Total with taxes and fees
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (3,357 reviews)
"The property itself is beautiful. I've stayed at a lot of hyatt hotels. The staff at this one were not polite or pleasant. I didn't encounter one nice staff member. The valet were the worse. This is one hotel that I would not stay at again."
Reviewed on Sep 17, 2025
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
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Special
Schiller Park, Illinois, USA
$14
$63 total
found 11 hours ago
Midsize
Schiller Park, Illinois, USA
$16
$66 total
found 11 hours ago
Standard
Schiller Park, Illinois, USA
$17
$69 total
found 11 hours ago
Premium Pickup Regular Cab
Schiller Park, Illinois, USA
$34
$112 total
found 14 hours ago
Lowest prices found within the past 11 hours. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
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.
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