Journey information
Overview: Waterloo, IN to Chicago, IL flight
Flights from Waterloo, IN to Chicago, IL depart on average 7 times per day, taking around 1h 22m. Cheap flight tickets for this journey start at $179 (€143) but you can travel from only $37 (€30) by train.
There are 7 flights per day. The earliest flight runs at 05:40, the last at 22:21. The fastest flight covers the 138 miles (223 km) distance in 1h 16m. March is the cheapest month to fly.
Distance 138 miles (223 km) |
Average flight duration 1h 22m |
Cheapest ticket price $179 (€143) |
Flights per day 7 |
Direct flights 7 |
Fastest flight 1h 16m |
First flight 5:40 AM |
Last flight 10:21 PM |
Cheapest Month Mar |
Cheapest Day Wed |
High Season Oct - Dec |
Low Season Jul - Sep |
Busiest Day Mon |
Least Busy Day Fri |
Best time to book 70 days |
The cheapest and fastest flights from Waterloo, IN to Chicago, IL
Cheapest price
$336
Average price
$351
Fastest journey
1 h 13 m
Average duration
1 h 20 m
Flights per day
5
Distance
223 km
The best way to find a cheap flight ticket from Waterloo, IN to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Waterloo, IN to Chicago, IL will cost around $351 if you buy it on the day, but the cheapest tickets can be found for only $336.
Of the 5 flights that leave Waterloo, IN for Chicago, IL onThu, May 07, 5 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Thu, May 07 the direct flights cover the 223 km distance in an average of 1 h 20 m but if you time it right, some flights will get you there in just 1 h 13 m .
On Thu, May 07 the longest flights will take 1 h 26 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
4:50 PM1h17Waterloo, IN6:07 PMChicago, IL$3361One-way0 transfers
9:45 PM1h25Waterloo, IN11:10 PMChicago, IL$3451One-way0 transfers
11:20 PM1h32Waterloo, IN12:52 AMChicago, IL$3461One-way0 transfers
10:49 AM1h13Waterloo, IN12:02 PMChicago, IL$3581One-way0 transfers
6:44 PM1h26Waterloo, IN8:10 PMChicago, IL$3681One-way0 transfers
10:49 AM1h13Waterloo, IN12:02 PMChicago, IL$3581One-way0 transfers
4:50 PM1h17Waterloo, IN6:07 PMChicago, IL$3361One-way0 transfers
11:00 AM1h19Waterloo, IN12:19 PMChicago, IL$3691One-way0 transfers
9:45 PM1h25Waterloo, IN11:10 PMChicago, IL$3451One-way0 transfers
6:44 PM1h26Waterloo, IN8:10 PMChicago, IL$3681One-way0 transfers
Travel Information
Compare train and flight for Waterloo, IN to Chicago, IL
Omio recommends booking the train as it is the most popular option from Waterloo, IN to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $37. For those with little time consider booking a flight which can get you there in 1h 22m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.1 - 0.2kg. The ticket price range depends on the travel mode: a train costs an average of $37, and a flight costs an average of $179.
Distance: 138 miles (223 km)
Compare flight with
| Flight | Most popular Train |
|---|---|
$320 Average price | $58 Average price Cheapest |
4h 22m Average total duration Fastest 1h 22m Onboard + 3h 0m Additional time* | 3h 47m Average total duration 3h 17m Onboard + 30m Additional time* |
0.7 - 1.3kg CO2 emissions | 0.1 - 0.2kg CO2 emissions Lowest |
Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
Live departures
Waterloo, IN to Chicago, IL flight times
The table below shows live departures for Waterloo, IN to Chicago, IL flights for today, Wednesday, May 6. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 12:05 PM Waterloo, IN | 1h21 | 1:26 PM Chicago, IL | 0 transfersDirect | |
![]() | 4:50 PM Waterloo, IN | 1h17 | 6:07 PM Chicago, IL | 0 transfersDirect | |
![]() | 9:45 PM Waterloo, IN | 1h21 | 11:06 PM Chicago, IL | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Waterloo, IN to Chicago, IL by train or flight
Compare train and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
May 07
May 08
May 09
May 10
May 11
May 12
May 13
FAQs: Waterloo, IN to Chicago, IL Flight
Find answers to the most common questions about traveling from Waterloo, IN to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

- Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan
- Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park
- Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.
- Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
- Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
- Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
- Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
- Field Museum, a natural history museum with vast exhibits including the famous T. rex skeleton, Sue.
- Memorial Day, the unofficial start of summer with vibrant outdoor activities and events
- Independence Day, spectacular fireworks and festive celebrations throughout the city
- Labor Day, a lively atmosphere with various festivals and pleasant weather.
- Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
- Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
- Take a river cruise to see the city's iconic architecture from a different perspective
- Attend a live performance at the historic Chicago Theatre
- Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U.S., offering free admission.
popular airports
Popular airports from Waterloo, IN to Chicago, IL
- Free Wi-Fi available throughout the airport.
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
- Available outside the terminal.
- Elevators, ramps, toilets
- Available throughout the airport.
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
- Lounges available, including United Club and American Airlines Admirals Club.
- Lost and Found located in terminal 1, near the baggage claim area.
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis.
- CTA Blue Line, O'Hare Station, 45 minutes to city center
More options for your journey from Waterloo, IN to Chicago, IL
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