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 $56 and $29 for one-way flights to Chicago for the period specified. Prices and availability are subject to change. Additional terms apply
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 3 days ago
$56
Roundtrip
found 3 days ago
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | Chicago | April 23 to April 27 | $56 |
| ATL | Chicago | April 21 to April 21 | $59 |
| ATL | Chicago | April 25 to April 25 | $68 |
| LAX | Chicago | April 28 to May 2 | $78 |
| EWR | Chicago | April 23 to April 27 | $99 |
| LAX | Chicago | May 2 to May 5 | $176 |
| EWR | Rockford | April 25 to April 28 | $184 |
| ATL | Rockford | May 27 to June 2 | $196 |
| LAX | Rockford | April 23 to April 28 | $220 |
| PEK | Chicago | May 20 to August 26 | $1,026 |
| PVG | Chicago | May 18 to August 16 | $1,098 |
| CAN | Chicago | May 20 to October 17 | $1,204 |
| XIY | Chicago | April 13 to April 20 | $1,414 |
| PVG | Chicago | June 13 to July 31 | $2,154 |
| HKG | Chicago | April 18 to April 19 | $2,447 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| DFW | Chicago | April 11 to May 6 | $114 |
| ATL | Chicago | April 11 to April 25 | $125 |
| ATL | Chicago | April 10 to April 18 | $158 |
| LGA | Chicago | April 12 to April 21 | $166 |
| DFW | Chicago | April 11 to April 15 | $166 |
| EWR | Chicago | April 11 to April 14 | $209 |
| LAX | Chicago | April 11 to April 14 | $218 |
| LGA | Rockford | April 10 to April 15 | $300 |
| LAX | Chicago | April 11 to April 13 | $302 |
| ATL | Rockford | April 12 to April 15 | $423 |
| HKG | Chicago | April 11 to May 7 | $1,067 |
| CAN | Chicago | April 12 to April 30 | $1,469 |
| PVG | Chicago | April 10 to May 20 | $2,051 |
| PEK | Chicago | April 12 to April 16 | $2,061 |
| HKG | Chicago | April 12 to April 13 | $4,595 |
Chicago Flight Information
Traveling to | Chicago |
|---|---|
Lowest Price | $56 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, 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
$78 nightly
The price is $92 total per night from Apr 14 to Apr 15
$92 total
Apr 14 - Apr 15
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (2,845 reviews)
The staff was so unprofessional with a bad attitude that he didn't let me sign the paper saying the exact check out time. One of the roomate smells bad and there wasn't windows that can be opened so I had to stay with the bad smell for whole day
Reviewed on Apr 3, 2026
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
$110 nightly
The price is $129 total per night from Apr 5 to Apr 6
$129 total
Apr 5 - Apr 6
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 ...
7.4/10 Good! (2,546 reviews)
Room and bathroom were clean and we had no issues
Reviewed on Apr 4, 2026
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 Apr 26 to Apr 27
$62 total
Apr 26 - Apr 27
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 ...
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Ohio House Motel
600 N La Salle Drive Chicago IL
$87 nightly
The price is $102 total per night from Apr 5 to Apr 6
$102 total
Apr 5 - Apr 6
Total with taxes and fees
Stay at this motel in Chicago. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff and the convenient parking ...
9/10 Wonderful! (1,091 reviews)
The Motel was very clean and very updated! The bed was extremely comfortable! Great location for walking. Employees were very friendly and extremely helpful! Great little place to stay!
Reviewed on Apr 3, 2026
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
$86 nightly
The price is $97 total per night from May 5 to May 6
$97 total
May 5 - May 6
Total with taxes and fees
Book a 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 ...
7.6/10 Good! (1,631 reviews)
Very good
Reviewed on Apr 2, 2026
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
777 E Grand Avenue Bensenville IL
$95 nightly
The price is $106 total per night from Apr 26 to Apr 27
$106 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.4/10 Good! (1,333 reviews)
Overall it was good, AC didn’t work well
Reviewed on Apr 4, 2026
Hampton Inn Chicago-O'Hare International Airport
3939 N Mannheim Rd Schiller Park IL
$104 nightly
The price is $120 total per night from Apr 5 to Apr 6
$120 total
Apr 5 - Apr 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 ...
9.2/10 Wonderful! (2,255 reviews)
Everything was great
Reviewed on Apr 3, 2026
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Holiday Inn Chicago O'Hare Area by IHG
5615 North Cumberland Avenue Chicago IL
$109 nightly
The price is $128 total per night from Apr 12 to Apr 13
$128 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.2/10 Very Good! (1,004 reviews)
Didn’t use
Reviewed on Apr 4, 2026
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
$371 nightly
The price is $436 total per night from Apr 12 to Apr 13
$436 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this 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! (1,849 reviews)
Highly recommend a stay here! The staff are amazing and the restaurant is incredible; get the French toast.
Reviewed on Apr 4, 2026
The Langham, Chicago
330 North Wabash Avenue Chicago IL
$435 nightly
The price is $511 total per night from Apr 26 to Apr 27
$511 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.8/10 Exceptional! (1,000 reviews)
I got the club suite and everything was beautiful and perfect. It was very clean and the walk in closet was awesome.
Reviewed on Apr 1, 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
$504 nightly
The price is $592 total per night from Apr 5 to Apr 6
$592 total
Apr 5 - Apr 6
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9.8/10 Exceptional! (1,001 reviews)
Awesome staff and over the top wonderful staff
Reviewed on Mar 30, 2026
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The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
521 North Rush Street Chicago IL
$304 nightly
The price is $357 total per night from Apr 5 to Apr 6
$357 total
Apr 5 - Apr 6
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (1,001 reviews)
Well connected and close to everything. Comfortable room. Would suggest that Tea/coffee machine should be included as standard in the room - it is available on request.
Reviewed on Apr 2, 2026
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
$136 nightly
The price is $160 total per night from Apr 12 to Apr 13
$160 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this 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! (2,803 reviews)
Over crowd, elevators not working , busy
Reviewed on Apr 3, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
$209 nightly
The price is $241 total per night from Apr 26 to Apr 27
$241 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,347 reviews)
The hotel main lobby is so beautiful! The pool was great and warm for the cold weather. Everything is walking distance.
Reviewed on Apr 3, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$135 nightly
The price is $159 total per night from Apr 12 to Apr 13
$159 total
Apr 12 - Apr 13
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,816 reviews)
It's a good hotel - but it can be very crowded. Expect long lines/waits for the elevator and breakfast. We were there end of March / beginning of April and the pool was so crowded we could not use it.
Reviewed on Apr 4, 2026
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Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
$244 nightly
The price is $286 total per night from Apr 6 to Apr 7
$286 total
Apr 6 - Apr 7
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,475 reviews)
This hotel is great! Great location, great staff.
Reviewed on Apr 3, 2026
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.
Chicago flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Special
Schiller Park, Illinois, USA
$15
$64 total
found 1 day ago
Midsize
Schiller Park, Illinois, USA
$16
$66 total
found 1 day ago
Standard
Schiller Park, Illinois, USA
$16
$68 total
found 1 day ago
Compact SUV
Schiller Park, Illinois, USA
$19
$76 total
found 1 day ago
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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