Cheap flights To Central Chicago (CHI) from $111

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Cheap Flights to Central Chicago from $111 One Way, $147 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Nov 3 - Sat, Nov 8
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select Air Canada flight, departing Mon, Nov 3 from Pearson Intl. to O'Hare Intl., returning Sat, Nov 8, priced at $147 found 2 days ago
Thu, Nov 6 - Tue, Nov 11
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select United flight, departing Thu, Nov 6 from Pearson Intl. to O'Hare Intl., returning Tue, Nov 11, priced at $147 found 2 days ago
Thu, Nov 6 - Tue, Nov 11
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Air Canada flight, departing Thu, Nov 6 from Pearson Intl. to O'Hare Intl., returning Tue, Nov 11, priced at $159 found 2 days ago
Thu, Nov 13 - Sun, Nov 16
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Nov 13 from Pearson Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $160 found 5 days ago
Sun, Sep 7 - Thu, Sep 11
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
$198 Roundtrip, just found
$198
Roundtrip
just found
Select Porter Airlines flight, departing Sun, Sep 7 from Billy Bishop Toronto City to Midway Intl., returning Thu, Sep 11, priced at $198 just found
Sat, Sep 13 - Sat, Sep 13
YYZ
Pearson Intl.
ORD
O'Hare Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 13 from Pearson Intl. to O'Hare Intl., returning Sat, Sep 13, priced at $198 found 1 day ago
Thu, Nov 13 - Sun, Nov 16
YTZ
Billy Bishop Toronto City
ORD
O'Hare Intl.
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Select Air Canada flight, departing Thu, Nov 13 from Billy Bishop Toronto City to O'Hare Intl., returning Sun, Nov 16, priced at $208 found 5 days ago
Sat, Sep 27 - Tue, Oct 14
YYZ
Pearson Intl.
MDW
Midway Intl.
$212 Roundtrip, found 6 days ago
$212
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Sep 27 from Pearson Intl. to Midway Intl., returning Tue, Oct 14, priced at $212 found 6 days ago
Thu, Nov 13 - Sun, Nov 16
YTZ
Billy Bishop Toronto City
MDW
Midway Intl.
$251 Roundtrip, found 5 days ago
$251
Roundtrip
found 5 days ago
Select Air Transat flight, departing Thu, Nov 13 from Billy Bishop Toronto City to Midway Intl., returning Sun, Nov 16, priced at $251 found 5 days ago
Sat, Jul 26 - Tue, Jul 29
TLC
Toluca Intl.
MDW
Midway Intl.
$264 Roundtrip, found 4 days ago
$264
Roundtrip
found 4 days ago
Select Volaris flight, departing Sat, Jul 26 from Toluca Intl. to Midway Intl., returning Tue, Jul 29, priced at $264 found 4 days ago

Central Chicago ORD Flight Information

Traveling To
Central Chicago
Destination Airport IATA Code
CHI
Number of Airlines Serving
16
Airlines
Air Canada, Porter Airlines, Viva, United, Delta, Air Transat, Volaris, American Airlines
Flight Price
$147
Earliest Departing Flight
AA 4487 6:03AM EDT
Latest Departing Flight
BA 5338 Jul 29 9:14PM EDT

Flights Review

Mar 10, 2018

Great overall service. Smooth landing. Plane was even early.

A verified traveler
Denver to Chicago · United

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Central Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
4.0-star property

Palmer House a Hilton Hotel

Sep 4 - Sep 8

4 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

Sep 4 - Sep 8

4 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Sep 8 - Sep 13

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 7 hours ago
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Central Chicago premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
4.0-star property

Palmer House a Hilton Hotel

8.4/10 Very Good! (1,773 reviews)

Sep 4 - Sep 8

4 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
per person
found 1 day ago
Old school, nice and clean

Reviewed on Jun 21, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,122 reviews)

Aug 22 - Aug 26

4 night stay

Dallas (DFW) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 24 hours ago
Modern, clean, great location that’s a short walk away from Magnificent Mile and the river. Will definitely book again.

Reviewed on Jul 21, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,635 reviews)

Sep 4 - Sep 8

4 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

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Central Chicago first class flight packages

Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
4.0-star property

Staypineapple, An Iconic Hotel, The Loop

9.4/10 Exceptional! (1,011 reviews)

Aug 29 - Sep 1

3 night stay

Minneapolis (MSP) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
per person
found 1 day ago
We again enjoyed our stay at the Pineapple!

Reviewed on Mar 18, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,000 reviews)

Aug 29 - Sep 1

3 night stay

Minneapolis (MSP) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,785 reviews)

Aug 29 - Sep 1

3 night stay

Minneapolis (MSP) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
per person
found 1 day ago
Fantastic stay, amazing location.

Reviewed on Jun 25, 2025

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Central Chicago

If you are looking for discount prices on flights to Central Chicago then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking Central Chicago flights easy and affordable.

Booking Made Easy

With Orbitz’s Display Matrix, booking flights to Central Chicago is simple. Just one glance gives you all the pricing information you need, including your discounts and savings. View all your options before selecting and booking your perfect Central Chicago flights.

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By using Orbitz’s free apps for iPhone and Android, and an easy-to-use mobile browser at m.orbitz.com, booking flights to Central Chicago has never been so convenient. Check for updates and alerts wherever you are, or manage your booking quickly. And we also offer mobile exclusive deals on hotels, so don’t delay—book right away.

The Complete Package

Orbitz makes it stress-free to book Central Chicago flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to Central Chicago, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.

Low Price Guarantee

Booking your Central Chicago flights with Orbitz guarantees low prices every day, all day—no matter when and where you book. You will always find the best deals available, coupled with extra great savings and discounts for all around great value.

Frequently asked questions

How much is a flight to Central Chicago?
Round-trip prices fell as low as $147 this week to Central Chicago, and rose to a high of $264. A few lucky passengers journeying out of Toronto (YYZ) managed to snare one-way fares from just $111.
How to book the cheapest flight to Central Chicago?
With Orbitz, you'll uncover some of the best flight deals around from a great range of airlines. But if you're eager to heighten your chances of snapping up cheap flights to Central Chicago, here are some suggestions to bear in mind:

  • Taking off from or arriving at other airports can often be cheaper. Enter your preferred departure and arrival points. Next, select the 'Nearby airports' function below to look through your options.
  • If you're flexible with your travel schedule, click on the 'Show flexible dates' link. It'll display the flight deals for the days around your chosen departure. Airfares often vary depending on what day of the week it is.
  • Select 'Show options' to narrow down your search results. You can pick your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even select whether you want to fly in the morning, afternoon or evening.
  • Once you've worked out your travel dates, don't wait to book. Prices normally increase as the departure date nears.
  • Bundle your flights, hotels and car rental into a package deal and enjoy discounts. Save your dollars for things that really excite you, like exploring every corner of Central Chicago.
  • If it's an option, avoid flying during the busy season. Airfares are often at their most expensive during summer, school breaks and other vacation periods like Easter and Christmas.

How long is a flight to Central Chicago?
The USA is big, so that depends on where you're leaving from. To make things simple, we've selected three of the busiest routes to Central Chicago and listed their average flight times:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 40 minutes
  • Boston, MA (BOS-Logan Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 51 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to O'Hare Intl. Airport (ORD) - 2 hours and 13 minutes

What is the best time to book a flight to Central Chicago?
If possible, book your flights to Central Chicago in January. This is the best month to reserve low airfares, followed by February and August. With a little planning, you're sure to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Central Chicago?
Make a booking on a Tuesday, Wednesday or Saturday. Generally, these are the cheapest days to purchase seats to Central Chicago. The getaway of your dreams starts with an unbeatable flight deal!
What is the cheapest day of the week to fly to Central Chicago?
Think about departing early in the week if you want to score cheap flights to Central Chicago. Orbitz data from 2020 shows Monday is typically the cheapest day to take off, followed by Tuesday. Saturdays were shown to have the most expensive ticket prices. This is possibly because most travelers choose to start their break when the weekend rolls around.
What is the cheapest month to fly to Central Chicago?
Jet off in August if you're sticking to a budget. Orbitz data shows that this is generally the best month for cheap flights to Central Chicago. June is when ticket prices hit their peak.
Which airlines allow free cancellation?
We understand that plans can change and flexibility is important. That's why you can search for flights that have free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll show you fares more flexible than candy on a dashboard in summer!
What do I need for the flight to Central Chicago?
Nothing's more fun than flying off on an adventure, but it's smart to be prepared. The following top tips will help get your trip off to a smooth start:

  • Your travel documents are the most important things you'll need to take with you on your flight to Central Chicago. To avoid any dramas at the time of check-in, make sure that the information displayed on your ticket is correct and matches your government-issued ID.
  • Make time fly by even faster on your short flight by packing the right things. Think tasty snacks, a water bottle and entertainment. If you'd like your journey to Central Chicago to pass peacefully, toss some headphones or earplugs into your carry-on bag too.
  • It can get cool on the plane. If you'd prefer not to shiver your way through the flight, wear another layer of clothing.

How many direct flights are there to Central Chicago?
With roughly 2,332 direct flights every month, you'll be flying straight into Central Chicago and starting your next big adventure in no time. Some of the airlines that journey nonstop to Central Chicago include United Airlines, American Airlines and Delta Air Lines. Southwest Airlines, Spirit Airlines and Air Canada are other frequently booked options.
How do I get cheap first-class/business deals to Central Chicago?
There are ways of booking first or business-class tickets to Central Chicago that won't burn through your savings. Bag a seat in the pointy end of the plane for less with these great tips:

  • Flexibility is everything. By being open to other travel dates, you'll have a better chance of picking up a great deal on your airfares.
  • Low-cost airlines offer first or business-class seats at a fraction of the usual price. Give the full-service carriers a miss and check out these cheaper options.
  • Make the most of your airline's flight rewards program and upgrade your seat. You can also bid for an upgrade in an online auction if available.

What is the best time to go to Central Chicago?
Central Chicago is busy in March, May and June. If you plan to visit during these months, it would be wise to book in advance to ensure you snap up the greatest deals. Wondering what summer's like in Central Chicago? Average daily temperatures normally fluctuate between 65 ºF and 75 ºF. Like most places in the Northern Hemisphere, the summer season begins June 20 here.

Nearby

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.