- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Flights from Waterloo, IN to Chicago, IL depart on average 7 times per day, taking around 1h 21m. Cheap flight tickets for this journey start at €116 but you can travel from only €22 by train.
There are 6 flights per day. The earliest flight runs at 05:00, the last at 22:45. 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 21m |
Cheapest ticket price €116 |
Flights per day 7 |
Direct flights 6 |
Fastest flight 1h 16m |
First flight 5:00 AM |
Last flight 10:45 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 |
Cheapest price
€182
Average price
€210
Fastest journey
1 h 16 m
Average duration
1 h 21 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 €210 if you buy it on the day, but the cheapest tickets can be found for only €182.
Of the 5 flights that leave Waterloo, IN for Chicago, IL onThu, Aug 06, 5 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Thu, Aug 06 the direct flights cover the 223 km distance in an average of 1 h 21 m but if you time it right, some flights will get you there in just 1 h 16 m .
On Thu, Aug 06 the longest flights will take 1 h 23 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.










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 €22. For those with little time consider booking a flight which can get you there in 1h 21m. 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 €22, and a flight costs an average of €116.
Distance: 138 miles (223 km)
| Flight | Most popular Train |
|---|---|
€215 Average price | €47 Average price Cheapest |
4h 21m Average total duration Fastest 1h 21m Onboard + 3h 0m Additional time* | 3h 45m Average total duration 3h 15m 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.
This is compared to other travel options from Waterloo, IN to Chicago, IL:
A train is €168 less than a flight for this route with tickets for a flight from Waterloo, IN to Chicago, IL costing on average €215.
Other travel options to Chicago, IL take longer:
Train takes on average 3h 15m.
The table below shows live departures for Waterloo, IN to Chicago, IL flights for today, Tuesday, August 4. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 4:23 PM Waterloo, IN | 1h21 | 5:44 PM Chicago, IL | 0 transfersDirect | |
![]() | 5:35 PM Waterloo, IN | 1h23 | 6:58 PM Chicago, IL | 0 transfersDirect | |
![]() | 9:45 PM Waterloo, IN | 1h21 | 11:06 PM Chicago, IL | 0 transfersDirect | |
![]() | 10:42 PM Waterloo, IN | 1h20 | 12:02 AM Chicago, IL | 0 transfersDirect | |
![]() | 11:25 PM Waterloo, IN | 1h23 | 12:48 AM Chicago, IL | 0 transfersDirect | |
![]() | 12:30 AM Waterloo, IN | 1h16 | 1:46 AM Chicago, IL | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
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.
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
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.

Most Waterloo, IN to Chicago, IL flights use the Fort Wayne International Airport to O'Hare International Airport airport pair. Use this guide to compare Waterloo, IN and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Lost and found is available at the station.
Available at O'Hare International Airport: Parking, Taxis, WC.
Available at O'Hare International Airport: Car Rental.
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Here are some other resources that might have the information you need