- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Flights from Anaheim, CA to Chicago, IL depart on average 199 times per day, taking around 11h 19m. Cheap flight tickets for this journey start at $217 if you book in advance.
There are 22 flights per day. The earliest flight runs at 00:10, the last at 23:58. The fastest flight covers the 1731 miles (2786 km) distance in 4h 0m. September is the cheapest month to fly.
Distance 1731 miles (2786 km) |
Average flight duration 11h 19m |
Cheapest ticket price $217 |
Flights per day 199 |
Direct flights 22 |
Fastest flight 4h 0m |
First flight 12:10 AM |
Last flight 11:58 PM |
Cheapest Month Sep |
Cheapest Day Sun |
High Season Jan - Mar |
Low Season Jul - Sep |
Best time to book 14 days |
Omio recommends booking the train as it is the most popular option from Anaheim, CA to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from $217. For those with little time consider booking a flight which can get you there in 11h 19m. The ticket price range depends on the travel mode: a flight costs an average of $217, and a train costs an average of $238.
Distance: 1731 miles (2786 km)
| Flight | Most popular Train | Bus |
|---|---|---|
$296 Average price Cheapest | $412 Average price | $339 Average price |
14h 19m Average total duration Fastest 11h 19m Onboard + 3h 0m Additional time* | 43h 35m Average total duration 43h 5m Onboard + 30m Additional time* | 53h 0m Average total duration 52h 30m Onboard + 30m Additional time* |
Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Anaheim, CA to Chicago, IL:
A flight is $44 less than a bus for this route with tickets for a bus from Anaheim, CA to Chicago, IL costing on average $339.
A flight is $116 less than a train for this route with tickets for a train from Anaheim, CA to Chicago, IL costing on average $412.
Other travel options to Chicago, IL take longer:
Train takes on average 43h 5m.
Bus takes on average 52h 30m.
Compare train, bus, 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 Anaheim, CA 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 Anaheim, CA to Chicago, IL flights use the Los Angeles International Airport to O'Hare International Airport airport pair. Use this guide to compare Anaheim, CA 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