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, just found
$56
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | April 29 to May 4 | $56 |
| ATL | Chicago | April 9 to April 13 | $57 |
| EWR | Chicago | April 25 to May 2 | $58 |
| LAX | Chicago | May 6 to May 9 | $77 |
| EWR | Rockford | April 25 to April 28 | $148 |
| ATL | Rockford | April 30 to May 6 | $176 |
| LAX | Chicago | April 24 to April 30 | $190 |
| LAX | Rockford | May 2 to May 5 | $198 |
| CAN | Chicago | April 16 to April 20 | $832 |
| HKG | Chicago | April 15 to April 30 | $838 |
| PEK | Chicago | April 7 to April 21 | $934 |
| PVG | Chicago | April 1 to April 22 | $990 |
| CTU | Chicago | March 12 to March 16 | $1,113 |
| XIY | Chicago | May 26 to June 3 | $1,279 |
| HKG | Chicago | March 12 to March 16 | $2,002 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| EWR | Chicago | February 27 to March 3 | $136 |
| ATL | Chicago | March 1 to March 3 | $143 |
| JFK | Chicago | February 28 to March 10 | $182 |
| DFW | Chicago | February 28 to March 4 | $225 |
| DFW | Chicago | February 27 to April 25 | $242 |
| ATL | Chicago | March 1 to March 3 | $245 |
| LGA | Rockford | February 27 to February 28 | $305 |
| ATL | Rockford | February 28 to March 3 | $310 |
| DFW | Rockford | February 27 to February 28 | $355 |
| LAX | Chicago | February 28 to March 5 | $397 |
| LAX | Rockford | February 27 to March 4 | $555 |
| LAX | Chicago | March 1 to March 7 | $557 |
| CAN | Chicago | February 27 to April 5 | $1,028 |
| PVG | Chicago | February 28 to May 11 | $1,266 |
| PEK | Chicago | February 28 to March 11 | $1,333 |
Chicago Flight Information
Traveling to | Chicago |
|---|---|
Lowest Price | $56 |
Number of Airlines Serving | |
Airlines Serving | Frontier 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
$80 nightly
The price is $95 total per night from Feb 26 to Feb 27
$95 total
Feb 26 - Feb 27
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! (2,778 reviews)
No better place to stay in Downtown Chicago for the money, comfort and easy walking district for shopping or dinning or nightlife. Casino across the street for added fun if that’s your thing! Book it and you will be happy!
Reviewed on Feb 24, 2026
Travelodge by Wyndham Downtown Chicago
65 E Harrison St Chicago IL
$79 nightly
The price is $93 total per night from Feb 26 to Feb 27
$93 total
Feb 26 - Feb 27
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! (2,519 reviews)
Was a great stay
Reviewed on Feb 24, 2026
Motel 6 Elk Grove Village, IL - O'Hare
2881 Touhy Ave Elk Grove Village IL
$42 nightly
The price is $48 total per night from Mar 5 to Mar 6
$48 total
Mar 5 - Mar 6
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! (1,846 reviews)
My stay was relaxing. The staff was helpful and welcoming. I'm glad I stayed here. The rooms were clean and quiet. I checked in with Tiffany. She was very kind and made me feel valued as a guest. Thank You!!
Reviewed on Feb 22, 2026
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Ohio House Motel
600 N La Salle Drive Chicago IL
$74 nightly
The price is $87 total per night from Mar 1 to Mar 2
$87 total
Mar 1 - Mar 2
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! (1,070 reviews)
Room was clean and staff friendly and helpful. Room was extremely hot though
Reviewed on Feb 22, 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
$67 nightly
The price is $75 total per night from Mar 2 to Mar 3
$75 total
Mar 2 - Mar 3
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! (1,629 reviews)
There was no hot water for shower. Water is mild Luke warm which is no good for extremely cold weather outside. Mentioned to hotel staff earlier but they didn't fixed it.
Reviewed on Feb 22, 2026
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 Feb 26 to Feb 27
$101 total
Feb 26 - Feb 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! (1,285 reviews)
great
Reviewed on Feb 24, 2026
Hampton Inn Chicago-O'Hare International Airport
3939 N Mannheim Rd Schiller Park IL
$89 nightly
The price is $101 total per night from Mar 8 to Mar 9
$101 total
Mar 8 - Mar 9
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! (2,224 reviews)
Hotel very clean, 8-minute shuttle ride to airport, hotel staff accommodating and friendly.
Reviewed on Feb 24, 2026
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Holiday Inn Chicago O'Hare Area by IHG
5615 North Cumberland Avenue Chicago IL
$91 nightly
The price is $107 total per night from Mar 16 to Mar 17
$107 total
Mar 16 - Mar 17
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 ...
8/10 Very Good! (1,001 reviews)
Clean, close to the airport, wonderful restaurant/bar in hotel, very friendly front desk staff
Reviewed on Feb 25, 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 Mar 3 to Mar 4
$436 total
Mar 3 - Mar 4
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! (1,838 reviews)
We had a great stay!
Reviewed on Feb 23, 2026
The Langham, Chicago
330 North Wabash Avenue Chicago IL
$457 nightly
The price is $536 total per night from Mar 22 to Mar 23
$536 total
Mar 22 - Mar 23
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! (1,009 reviews)
Staff at check in was friendly and efficient. Rooms are spacious. Location couldnt be better and the on sight bar is wonderful
Reviewed on Feb 23, 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
$504 nightly
The price is $592 total per night from Mar 5 to Mar 6
$592 total
Mar 5 - Mar 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! (1,009 reviews)
First class staff and hotel !
Reviewed on Feb 24, 2026
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The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
521 North Rush Street Chicago IL
$237 nightly
The price is $278 total per night from Mar 20 to Mar 21
$278 total
Mar 20 - Mar 21
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. ...
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
$124 nightly
The price is $146 total per night from Mar 3 to Mar 4
$146 total
Mar 3 - Mar 4
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! (2,833 reviews)
The hotel was very clean and accommodating. The complementary breakfast was very good.
Reviewed on Feb 23, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
$176 nightly
The price is $202 total per night from Mar 6 to Mar 7
$202 total
Mar 6 - Mar 7
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! (2,317 reviews)
Beautiful hotel with exceptional service.
Reviewed on Feb 25, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
$103 nightly
The price is $120 total per night from Mar 3 to Mar 4
$120 total
Mar 3 - Mar 4
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! (5,683 reviews)
Stated 3 nights. Room clean and spacious. Breakfast was great. Elevators run a bit slow.
Reviewed on Feb 25, 2026
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Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
$213 nightly
The price is $250 total per night from Mar 25 to Mar 26
$250 total
Mar 25 - Mar 26
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! (3,492 reviews)
The room was spotless. The front desk helped make sure my reservation was taken care of despite travel delays outside of my control. Highly recommended this property and their staff
Reviewed on Feb 24, 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 - premium 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
$9
$50 total
found 1 day ago
Midsize SUV
Schiller Park, Illinois, USA
$12
$58 total
found 1 day ago
Compact SUV
Schiller Park, Illinois, USA
$14
$61 total
found 1 day ago
Standard
Schiller Park, Illinois, USA
$15
$65 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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