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$44+ Cheap flights from Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CUN
Jan 21 — Jan 281
Wed 1/21
Wed 1/28
1 adult, Economy
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What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated December 22, 2025.

Cheapest airline

Emirates

Good round-trip deal

$66 or less

Good one-way deal

$28 or less
On average, Emirates currently has the cheapest one-way flight from Chicago (avg. price of $1,162).
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Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Find flights from Chicago

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on December 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:40 amORD - JFK
Nonstop2h 24mFrontier
Sun 3/111:03 amJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/19$77
This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/98:35 amORD - JFK
Nonstop2h 24mFrontier
Wed 1/144:24 pmJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/22$79
This Flightnetwork deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/98:35 amORD - JFK
Nonstop2h 24mFrontier
Fri 1/164:24 pmJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/21$80
This Kiwi.com deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Wed 1/71:00 pmJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/21$82
This Frontier deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/56:40 amORD - JFK
Nonstop2h 24mFrontier
Fri 1/91:00 pmJFK - ORD
Nonstop2h 57mFrontier
Deal found 12/21$83
This Frontier deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/208:38 amORD - DFW
Nonstop2h 58mFrontier
Sun 2/225:01 amDFW - ORD
Nonstop2h 33mFrontier
Deal found 12/22$89
This Super.com deal was found by Cheapflights users on 12/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:40 amORD - JFK
Nonstop2h 24mFrontier
Fri 3/64:29 pmJFK - ORD
Nonstop3h 00mFrontier
Deal found 12/19$89
This Cheapflightsfares deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/49:23 amORD - DFW
1 stop14h 35mSpirit Airlines
Wed 2/117:30 amDFW - ORD
1 stop13h 33mSpirit Airlines
Deal found 12/22$90
This Expedia deal was found by Cheapflights users on 12/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/37:20 amORD - DFW
1 stop14h 03mSpirit Airlines
Tue 2/107:30 amDFW - ORD
1 stop13h 33mSpirit Airlines
Deal found 12/20$91
This Kiwi.com deal was found by Cheapflights users on 12/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/147:20 amORD - DFW
1 stop14h 03mMultiple Airlines
Thu 1/159:09 pmDFW - ORD
Nonstop2h 33mMultiple Airlines
Deal found 12/20$92
This CheapOair deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/27:20 amORD - MCO
1 stop5h 43mSpirit Airlines
Thu 2/53:43 pmMCO - ORD
Nonstop3h 09mSpirit Airlines
Deal found 12/22$92
This Priceline deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/710:07 amORD - FLL
1 stop8h 58mMultiple Airlines
Fri 2/138:27 pmFLL - ORD
Nonstop3h 36mMultiple Airlines
Deal found 12/22$93

Find flights from Chicago within your budget

 
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on December 22, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Cancún

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 1/30

10:48 am-2:38 pm

Nonstop2h 50m

Orlando

Fri 1/30

5:28 pm-7:41 pm

Nonstop3h 13m

$93

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sat 1/17

7:20 am-11:35 am

Nonstop3h 15m

Fort Lauderdale

Sat 1/17

9:25 pm-11:46 pm

Nonstop3h 21m

$94

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Tue 1/20

5:15 am-9:22 am

Nonstop3h 07m

Fort Lauderdale

Tue 1/20

9:25 pm-11:46 pm

Nonstop3h 21m

$104

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 1/19

12:44 pm-4:31 pm

Nonstop2h 47m

Orlando

Mon 1/26

5:28 pm-7:41 pm

Nonstop3h 13m

$113

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sat 1/17

5:32 pm-9:40 pm

Nonstop3h 08m

Fort Lauderdale

Tue 1/20

8:54 am-11:22 am

Nonstop3h 28m

$114

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Mon 1/19

5:32 pm-9:40 pm

Nonstop3h 08m

Fort Lauderdale

Thu 1/29

7:10 am-11:47 am

1 stop5h 37m

$120

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sun 1/18

8:43 pm-12:59 am

Nonstop3h 16m

Fort Lauderdale

Thu 1/22

12:11 pm-10:42 pm

1 stop11h 31m

$120

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Mon 1/12

12:44 pm-8:10 pm

1 stop6h 26m

Fort Lauderdale

Thu 1/15

7:10 am-11:47 am

1 stop5h 37m

$124

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Sat 1/17

2:30 pm-6:04 pm

Nonstop2h 34m

New York John F Kennedy Intl

Wed 1/21

11:20 am-1:14 pm

Nonstop2h 54m

$139

ChicagoNew York

ORD - JFK

ORDJFK

Chicago O'Hare Intl

Wed 1/28

1:57 pm-5:30 pm

Nonstop2h 33m

New York John F Kennedy Intl

Mon 2/2

3:52 pm-5:45 pm

Nonstop2h 53m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
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Compare providers for flights from Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago in December
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: Among all the travel providers offering deals on flights from Chicago, Mytrip has been found to have the most accurate pricing. Users can find the same prices on deals on Cheapflights as Mytrip about >95% of the time. This is based on searches for flights from Chicago made on Cheapflights over the past month and is updated monthly.
  • Most trusted provider: In terms of trustworthiness, Cheapflights users rate Mytrip the highest out of those offering flight deals from Chicago. Mytrip has a user feedback rating of 3 out of 3 stars (3 being the best) and has received the most positive sentiment from Cheapflights users searching for flights from Chicago. This info is gathered from Cheapflights searches over the past month.

Chicago travel tips

Get helpful tips and advice for traveling to or from Chicago. Find recommendations for transportation, accommodations, local attractions, dining options, and other practical tips to enhance your travel experience. Please note that the travel tips are based on general knowledge and recommendations. Data last updated December 22, 2025.
  • Chicago O' Hare International Airport (ORD) is a major hub for United Airlines, and because of this fact, passengers will find a number of direct flights from the airport to destinations both inside and outside of the United States.
  • For those passengers looking for a convenient way to get from downtown Chicago to Chicago O' Hare International Airport, the Blue Line provided by the Chicago Transit Authority can make this trip in about 42 min, plus it avoids any possible traffic congestion on roadways.
  • If you have a flight that is departing Chicago Midway International Airport, a great way to get to the airport from downtown Chicago is on the Orange Line light rail service provided by the Chicago Transit Authority that can make the trip to the airport in around 23 min.
  • If you plan on driving your own car to the Chicago O' Hare International Airport, one of the most convenient options for parking is their valet service. Passengers can utilize the service by taking their vehicle into the main garage for all three of the terminal buildings. Once in the garage, follow the signage for valet parking and then make your way to the designated area for your airline or terminal.
  • Visitors to the Chicago O'Hare International Airport (CHI) with some extra time on their hands are encouraged to explore the art exhibition in Terminal 5, which features works by more than 20 Chicago artists.
  • Those looking for a bite to eat at the Chicago O'Hare International Airport (CHI) will find hundreds of opportunities at their disposal ranging from vending machines and grab-and-go bites to well-known franchises like Dunkin Donuts to local food options like Chicago-Style Hot Dogs.
  • There are shopping opportunities a-plenty for visitors to the Chicago O'Hare International Airport (CHI). From cosmetics vending machines to well-known retailers like Brookstone to independent stores offering local souvenirs, there is no shortage of ways to treat yourself while waiting to board your flight.

Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

When is the best time to book a flight from Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Cancún. Price data was last updated on December 19, 2025.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 66 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago?

Currently, January is the cheapest month in which you can book a flight from Chicago (average of $137). Flying from Chicago in July will prove the most costly (average of $217). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Chicago?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Cancún. Price data was last updated on December 20, 2025.

Those who are seeking the cheapest fare on flights departing from Chicago would be wise to consider leaving during Wednesday at noon when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Thursday evenings when fares are usually the most expensive.

Which airlines fly from Chicago?

For flights departing from Chicago check dates and pricing for the following: United Airlines, American Airlines, Spirit Airlines, Frontier, Southwest. These airlines depart to the following popular destinations: Cancún.

United Airlines
United Airlines
From $90
American Airlines
American Airlines
From $91
Frontier
Frontier
From $37
Spirit Airlines
Spirit Airlines
From $36

What are popular destinations to fly to from Chicago?

Some of the most frequent flights departing from Chicago everyday are: Orlando (902 flights per day), New York (849 flights per day), and Detroit (798 flights per day).

New York
New York
From $33
Istanbul
Istanbul
From $440
Orlando
Orlando
From $47
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From $34

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Burlington, with prices starting at $28. Explore other affordable destinations below.

Burlington
Burlington
From $28
Miami
Miami
From $29
New York
New York
From $33
Tampa
Tampa
From $34

Airline reviews for flights from Chicago

Read reviews and ratings of airlines operating flights from Chicago. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Chicago travel. Please note that the reviews are sourced from user searches and were last updated on December 22, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Read through reviews of airlines servicing Chicago, such as Southwest, United Airlines, and American Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,105 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,196 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,075 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated December 22, 2025.

  • What are the most popular destinations to fly to from Chicago?

    This month, the top selected destinations from Chicago are Ahmedabad, Mumbai, Atlanta. Throughout the year, Atlanta, Boston, Ahmedabad are some of the top choices made by users flying from Chicago.

  • What is the cheapest airport to fly out of Chicago?

    Chicago O'Hare Intl airport offers the cheapest routes to Belize City, from $51; whereas Chicago Midway airport is typically cheaper if you're flying to Guatemala City, from $58. It's best to make sure you are flexible on dates to find the cheapest possible flight options for your journey.

  • What is the cheapest flight from Chicago to anywhere?

    Users have flown out of Chicago for as low as $112 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for $166 to fly from Chicago.

  • What are the cheapest airlines flying from Chicago to anywhere?

    Over the past few days, we've found that Emirates, Frontier, and Spirit Airlines have the cheapest prices from Chicago. Emirates flights from Chicago to Ahmedabad ($6), Frontier flights from Chicago to Aguascalients ($38), and Spirit Airlines flights from Chicago to Atlantic City ($48).

  • What is the cheapest month to fly from Chicago?

    January is currently the cheapest month to fly from Chicago. At this moment in time July is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Chicago?

    Check out the cheapest flights from Chicago to embark to:
    Fly from Chicago to Fort Lauderdale from $51 round trip
    Fly from Chicago to Miami from $51 round trip
    Fly from Chicago to Orlando from $58 round trip
    Fly from Chicago to Tampa from $58 round trip
    Fly from Chicago to Dallas from $59 round trip

  • If I am a parent traveling with children, what are some of the things I should know about the Chicago O' Hare International Airport?

    One of the great features of this airport is that it offers a Family Lounge that is just past the security checkpoint inside Terminal Two. This lounge features a designated space where kids can safely play, plus around this kid's play area, there is a wide variety of seating options that include charging stations for electronic devices plus space to park a stroller. At various times of the year, there's live entertainment in this area as well. This airport also features around six different mothers' rooms that allow mothers to tend to infants in a comfortable setting plus, the airport also features around 10 different lactation pods that offer a locking door and a comfortable space. Parents that make their way to the information desk at the airport can receive a free airport activity and coloring book that can keep kids occupied while at the airport.

  • What are some of the most comfortable places I can wait for a flight at the Chicago O' Hare International Airport?

    If you are a member of the military traveling from Chicago, this airport features a USO Lounge that is outside of the security checkpoints inside of Terminal Two. This lounge features amenities such as snacks and drinks, televisions, and computers with internet access, plus it has a great children's play area. Passengers aboard flights with American Airlines will find that this airport features four Admirals Club lounges in Terminal 3. All of these lounges offer comfortable seating choices, food and drinks, and internet access, and two of the lounges offer shower facilities. If you are a passenger on an international flight aboard British Airways, you will find this airline offers two lounges inside of Terminal Five that offer a great selection of dining and beverage choices and comfortable seating.

  • What are some of the ways I can pass the time before a flight from Chicago Midway International Airport (MDW)?

    One of the wonderful features of this airport is that they offer a yoga room that has a location on Concourse C right adjacent to the mother's room at the airport. This room offers a sustainable bamboo wood floor, plus they provide exercise mats and a location to put your personal articles and garments. Passengers often use the space for meditation, relaxation, and yoga practice before a flight. The room features frosted glass windows to allow in light yet keep privacy for users. Another way to pass the time is to experience the public art program at the airport. This is a collection of artwork that features dozens of paintings, mules, sculptors, and exhibits that have locations throughout all of the buildings at the airport.

  • Are there overnight accommodations available at the Chicago O'Hare International Airport (CHI)?

    Yes, the Chicago O'Hare International Airport (CHI) is home to the Hilton Chicago O’Hare Airport Hotel, which is located across from Terminals 1, 2, and 3. You will need to take the Airport Transit System if coming from Terminal 5, but Terminals 1, 2, and 3 are connected within walking distance by underground walkways.

  • Are there designated spaces for children at the Chicago O'Hare International Airport (CHI)?

    Yes, the Chicago O'Hare International Airport (CHI) provides colorful seating, stroller parking, device charging stations, and even live entertainment in the Family Lounge, located in Terminal 2 just beyond security.

  • Does the Chicago O'Hare International Airport (CHI) offer any unique amenities for visitors?

    Yes, the Chicago O'Hare International Airport (CHI) offers a Yoga Room on the Mezzanine Level of Terminal 3 for visitors wanting to escape the excitement of the airport.

  • Does the Chicago O'Hare International Airport (CHI) offer transportation between terminals?

    Yes, the Chicago O'Hare International Airport (CHI) offers an Airport Transit System (ATS) between Terminal 5 and the other terminals. If you’re looking to move amongst Terminals 1, 2, and 3, you do not need to leave the secured side of the airport. Signage will guide you from one domestic terminal to the next.

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