ALO - ORD

$350 Find Cheap Flights from Waterloo to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Waterloo to O'Hare Intl departing on 5/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Waterloo to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Waterloo to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Waterloo to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Waterloo to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Waterloo to O'Hare Intl

KAYAK's recommended round-trip deals from the most popular airlines that fly from Waterloo to O'Hare Intl.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
6:00 am - 7:21 amALO-ORD
1h 21mnonstop
American Airlines Logo
1:30 pm - 2:41 pmORD-ALO
1h 11mnonstop
$371American Airlines
Find Deal
Thu, Aug 14 - Sun, Aug 17
American Airlines Logo
6:08 am - 7:30 amALO-ORD
1h 22mnonstop
American Airlines Logo
8:50 pm - 10:07 pmORD-ALO
1h 17mnonstop
$468American Airlines
Find Deal
Wed, May 14 - Sun, May 18
American Airlines Logo
6:08 am - 7:30 amALO-ORD
1h 22mnonstop
American Airlines Logo
8:50 pm - 10:07 pmORD-ALO
1h 17mnonstop
$489American Airlines
Find Deal
Thu, May 15 - Mon, May 19
Useful Info

KAYAK's insights & trends for Waterloo to O'Hare Intl flights

Get data-powered insights and trends into flights from Waterloo to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Waterloo to Chicago?

The average price of all round-trip flights from Waterloo to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Waterloo to Chicago, look for departures on Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago, Saturday is the cheapest day to fly and Thursday is the most expensive.

Can I save money by flying with a layover from Waterloo to Chicago O'Hare Intl Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $308 on average.

Good to know

Cheapest flight$350
Flight from Waterloo to Chicago

When to book flights from Waterloo to O'Hare Intl

Are your dates flexible? Find out the best times to travel from Waterloo to O'Hare Intl based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Waterloo to Chicago flights

  • What is the cheapest flight from Waterloo to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Waterloo to Chicago O'Hare Intl Airport was $350 for a one-way ticket and $371 for a round-trip.

  • Do I need a passport to fly between Waterloo and Chicago?

    No, a passport isn't needed to fly from Waterloo to Chicago. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Waterloo to Chicago?

    Waterloo and Chicago are both served by 1 main airport. You will leave Waterloo from Waterloo and will be arriving at Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Waterloo to Chicago?

    Only American Airlines offers inflight Wi-Fi service on the Waterloo to Chicago flight route.

  • Which aircraft models fly most regularly from Waterloo to Chicago?

    The Airbus A319 is the aircraft model that flies most regularly on the Waterloo to Chicago flight route.

  • Which airline alliances offer flights from Waterloo to Chicago?

    oneworld is the only airline alliance operating flights between Waterloo and Chicago.

  • On which days can I fly direct from Waterloo to Chicago?

    There are nonstop flights from Waterloo to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Waterloo to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Waterloo to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Waterloo to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Waterloo is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Waterloo to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Waterloo with another airline. Booking your flights between Waterloo and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Waterloo to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Waterloo up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Waterloo to Chicago O'Hare Intl Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $254 or less one-way and $373 or less round-trip.

Prefer to fly direct from Waterloo to Chicago?

Find which airlines fly direct from Waterloo Airport to Chicago O'Hare Intl Airport, which days they fly and book direct flights.

Direct departures

Waterloo to Chicago O'Hare Intl

Monday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Tuesday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Wednesday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Thursday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Friday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Saturday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Sunday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

See more direct flights

Direct returns

Chicago O'Hare Intl to Waterloo

Monday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Tuesday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Wednesday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Thursday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Friday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Saturday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

Sunday

American Airlines, Qatar Airways

American Airlines, Qatar Airways

See more direct flights
See more direct flights

Top airline flying from Waterloo to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying from Waterloo to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Waterloo to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 10000 reviews
6.5Food
7.5Boarding
8.0Crew
7.2Comfort
6.9Entertainment
Airline reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

2.0 MediocreAnonymous, Apr 2025SDF - ORD
Read more American Airlines reviews

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

Everything you need to know for your flight from Waterloo to O'Hare Intl

Information on your arrival and departure airports

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