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Cheap flights from Waterloo, Iowa to Chicago from $149

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Waterloo, Iowa to Chicago departing on 8/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Waterloo, Iowa to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:00 am - 6:24 am
ALO
-
ORD
1h 24mnonstop
American Airlines Logo
1:06 pm - 2:30 pm
ORD
-
ALO
1h 24mnonstop
$203American Airlines
Wed, Jun 24 - Wed, Jul 1
American Airlines Logo
3:00 pm - 4:34 pm
ALO
-
ORD
1h 34mnonstop
American Airlines Logo
12:59 pm - 2:23 pm
ORD
-
ALO
1h 24mnonstop
$204American Airlines
Thu, Jun 25 - Sun, Jun 28
American Airlines Logo
3:00 pm - 4:34 pm
ALO
-
ORD
1h 34mnonstop
American Airlines Logo
11:00 pm - 12:21 am
ORD
-
ALO
1h 21mnonstop
$245American Airlines
Thu, Jun 11 - Sun, Jun 14
American Airlines Logo
5:00 am - 6:22 am
ALO
-
ORD
1h 22mnonstop
American Airlines Logo
11:00 pm - 12:21 am
ORD
-
ALO
1h 21mnonstop
$274American Airlines
Mon, Jun 1 - Mon, Jun 8
American Airlines Logo
3:00 pm - 4:34 pm
ALO
-
ORD
1h 34mnonstop
American Airlines Logo
11:00 pm - 12:21 am
ORD
-
ALO
1h 21mnonstop
$304American Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
3:26 pm - 5:00 pm
ALO
-
ORD
1h 34mnonstop
American Airlines Logo
11:07 pm - 12:29 am
ORD
-
ALO
1h 22mnonstop
$318American Airlines
Fri, Jul 24 - Tue, Jul 28

American Airlines flights from Waterloo, Iowa to Chicago

Our best American Airlines deals on Waterloo, Iowa to Chicago flight tickets
American Airlines
Jun 24
ALO5:00 amWaterloo
1h 24m
ORD6:24 amChicago O'Hare Intl
Jul 1
ORD1:06 pmChicago O'Hare Intl
1h 24m
ALO2:30 pmWaterloo
$203
American Airlines
Jun 25
ALO3:00 pmWaterloo
1h 34m
ORD4:34 pmChicago O'Hare Intl
Jun 28
ORD12:59 pmChicago O'Hare Intl
1h 24m
ALO2:23 pmWaterloo
$204
American Airlines
Jun 11
ALO3:00 pmWaterloo
1h 34m
ORD4:34 pmChicago O'Hare Intl
Jun 14
ORD11:00 pmChicago O'Hare Intl
1h 21m
ALO12:21 amWaterloo
$245

momondo Fare Finder

 
Customize your flight search to find flights from Waterloo, Iowa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated May 28, 2026.
Use the filters below to find and compare flights from Waterloo, Iowa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Wed 6/24

5:00 am-6:24 am

Nonstop1h 24m

Chicago O'Hare Intl

Wed 7/1

1:06 pm-2:30 pm

Nonstop1h 24m

$203

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Thu 6/25

3:00 pm-4:34 pm

Nonstop1h 34m

Chicago O'Hare Intl

Sun 6/28

12:59 pm-2:23 pm

Nonstop1h 24m

$204

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Thu 6/11

3:00 pm-4:34 pm

Nonstop1h 34m

Chicago O'Hare Intl

Sun 6/14

11:00 pm-12:21 am

Nonstop1h 21m

$245
Quickest round-trip

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Mon 6/1

5:00 am-6:22 am

Nonstop1h 22m

Chicago O'Hare Intl

Mon 6/8

11:00 pm-12:21 am

Nonstop1h 21m

$274

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Fri 6/5

3:00 pm-4:34 pm

Nonstop1h 34m

Chicago O'Hare Intl

Mon 6/8

11:00 pm-12:21 am

Nonstop1h 21m

$304

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Fri 7/24

3:26 pm-5:00 pm

Nonstop1h 34m

Chicago O'Hare Intl

Tue 7/28

11:07 pm-12:29 am

Nonstop1h 22m

$318
Cheapest one-way
Quickest one-way

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Thu 8/20

5:00 am-6:23 am

Nonstop1h 23m

$149

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Fri 11/20

6:00 am-7:30 am

Nonstop1h 30m

$169

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Chicago from

How to get the cheapest flight ticket from Waterloo, Iowa to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $440. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Waterloo, Iowa to Chicago for around $614.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Waterloo, Iowa to Chicago during this time can be as low as $479. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $589.

What is the cheapest Waterloo to Chicago flight route?

Fly from Waterloo to Chicago O'Hare Intl for the best Waterloo - Chicago flight prices

What cabin class options are available on Waterloo, Iowa to Chicago flights?

There are 4 cabin classes available to choose from on Waterloo, Iowa to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

When to book flights from Waterloo, Iowa to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Waterloo, Iowa to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Waterloo, Iowa to Chicago (ALO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Waterloo, Iowa to Chicago

Best Price Found

$316

Fastest flight time

1h 22m

Direct flights

Thu, Fri and Sat

Airports in Chicago

3 airports
The best one-way flight to Chicago from Waterloo, Iowa in the past 72 hours is $316. The best round-trip flight deal from Waterloo, Iowa to Chicago found on momondo in the last 72 hours is $523.
The fastest flight from Waterloo, Iowa to Chicago takes 1h 22m
Direct flights go from Waterloo, Iowa to Chicago on Thursday, Friday and Saturday. The only airline offering direct flights is American Airlines.
There are 3 airports in Chicago. From Waterloo, Iowa there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Waterloo, Iowa to Chicago

  • How far is Waterloo to Chicago by plane?

    There are 245.0 mi between Waterloo and Chicago. Flights usually cover this in 1h 22m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Waterloo Airport to Chicago?

    Prices for flights from Waterloo Airport to Chicago are updated daily.

  • How old do you have to be to fly from Waterloo Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Waterloo Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Waterloo, Iowa to Chicago?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Waterloo to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Waterloo to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Waterloo to Chicago with flexible booking policies on momondo?

Flights from Waterloo to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Waterloo to Chicago?

Once all potential Waterloo to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Waterloo to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Waterloo. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport