Cheap Flights from Redmond (RDM) to Chicago (CHIA)

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Flight deals from Redmond to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Redmond to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

Find the cheapest month to fly from Redmond to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Redmond to Chicago flights are currently cheapest in August.

Alternative Redmond to Chicago routes

Looking for the cheapest, fastest or easiest route from Redmond to Chicago? You could fly into the following airports instead.

Redmond to Chicago: Flight information

The things to know before you go.
Cheapest flight found$131
Cheapest month to flyAugust

Finding cheap flights from Redmond to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Redmond to Chicago is $232. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Redmond to Chicago. But we found flights with one or more stops from $232.
There are no flights flying from Redmond to Chicago, as of May 2025.
The cheapest month to fly from Redmond to Chicago is usually May 2025.
If you're flying from Redmond Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the center of Chicago. We've found flights to this airport from $232.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Redmond Airport to Chicago on Friday, July 4, 2025.
No airlines currently offer direct flights between Redmond Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 56°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.
Currently, Alaska Airlines offers the cheapest flight tickets to Chicago.

Traveling from Roberts Field Airport (RDM) to Chicago: what you need to know

  • The timezone in Chicago is UTC-5. The city is two hours ahead of Redmond, where Roberts Field Airport is located.

  • For a relaxed start to your RDM to Chicago flight, leave enough time for things like baggage drop and finding your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the general rule.

  • Taking off during a peak time like school or public holidays? Expect longer lines at security and check-in. To give yourself peace of mind, arrive up to four hours before international flights and two hours ahead of domestic departures.

  • The journey from central Redmond to RDM takes around 50 minutes on public transport. If you ride-share, drive or take a cab, you'll cover the 2 miles in 10 minutes or so, depending on traffic.

  • Booked an early flight from Roberts Field Airport to Chicago? Avoid rushing to the airport (and sneak in some extra snooze time) by choosing one of these hotels near RDM:

  • Of all flights leaving Roberts Field Airport, 76.41% arrive as scheduled at their destination.

How to find the cheapest flights from Roberts Field Airport (RDM) to Chicago

  • $131 is the cheapest price we've seen for a one-way Roberts Field Airport to Chicago flight. A return ticket right now is $232. Depending on when you book and the availability, these fares may change.

  • Don't wait until the last moment. You're more likely to land cheap flights from RDM to Chicago if you book ahead. Airlines often have some fantastic early bird rates.

  • If you can be flexible with your travel plans, try using the 'Whole month' search tool. It'll show you the cheapest price across every month when searching for your Roberts Field Airport to Chicago ticket.

  • There's no need to check every day to see if fares have dropped when you set up a Price Alert. We'll update you when there's an extra saving on cheap flights from RDM to Chicago.

  • Pick your preferred arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Roberts Field Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 25 miles. It takes about 35 minutes to get to the center driving.

  • If you're traveling by public transport, expect a journey time of about 55 minutes.

  • The last thing you want is a lengthy journey to your hotel if you're getting in late on a flight from Roberts Field Airport to Chicago. Reserve one of these accommodation options near ORD instead:

  • Explore without limits with an O'Hare International Airport rental car. Pick up your wheels from Routes Car Rentals, Dollar or Budget and experience more of Chicago and beyond.

  • Booking your vehicle from O'Hare International Airport around four weeks before your flight from RDM to Chicago can help you lock in the lowest rate.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Roberts Field Airport to Chicago has touched down, you can get to the city center in around 20 minutes by car. Central Chicago is roughly 12 miles from Chicago Midway International Airport (MDW).

  • If you travel by public transport, the journey will take you 45 minutes or so.

  • You'll find some comfortable places to call home for the night near MDW. Settle in and get cozy after your RDM to Chicago flight at any of these perfectly located options:

  • The fastest way to reach your destination is with a Chicago Midway International Airport rental car. Pick up your wheels from Dollar, Hertz or Budget and be on your way in a flash.

  • Get the lowest price by booking your ride from MDW four weeks ahead of time. You'll also have access to a greater selection of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 85 miles from the center of Chicago. It takes about 1 hour 25 minutes to get to the city center by cab or ride-share once you've stepped off your flight from Roberts Field Airport to Chicago.

  • If you travel by public transport, the journey time is about 4 hours 15 minutes.

  • Enjoy a low-stress, comfortable start to your break by staying at a hotel near RFD after your RDM to Chicago flight. Rest up after a long day of travel or simply take a moment to get your bearings in a new destination at:

  • Begin your journey without worrying about how to reach your next stop with a Chicago Rockford International Airport rental car. You can book with reliable companies here like Budget, Alamo and National.

  • If you're looking for a particular kind of vehicle, booking early gives you a better shot at getting exactly what you want. Secure your ride from RFD at least a couple of weeks ahead of your flight from Roberts Field Airport to Chicago.

  • Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • Before securing your flights from Roberts Field Airport to Chicago, consider which time of year is best for you. Peak season in Chicago offers a bustling atmosphere and plenty of activities, while low season means you'll get better deals on hotels and fewer crowds.

  • Before locking in your Roberts Field Airport to Chicago plane ticket, think about the weather you're most comfortable in. July is the warmest month in Chicago, with temperatures ranging from 59ºF to 84ºF.

  • For cooler conditions, search for a cheap ticket from RDM to Chicago in January when temperatures average between 10ºF and 37ºF.

More about Chicago

  • Once you've booked your flight from Roberts Field Airport to Chicago, find a hotel that offers both comfort and a great location. Make one of these options your base for exploring Chicago:

  • There are so many things to see and do in this city it can be hard to figure out where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are leading attractions which should be on every Chicago itinerary.

Explore more of United States

  • You've visited Chicago, now it's time to discover other parts of United States. Travel about 280 miles south-east to Columbus to check off its top attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you'll have a packed itinerary ahead.

  • Around 160 miles south-east of Chicago, Indianapolis is another essential stop in United States. Experience the best of this destination with a visit to The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.