GRR - CHI

$49 Find Cheap Flights from Grand Rapids to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Grand Rapids to Chicago departing on 10/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Grand Rapids to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Grand Rapids to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Grand Rapids to Chicago (GRR-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Grand Rapids to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Grand Rapids to Chicago

Do, Okt 9 - Mo, Okt 13
Southwest Logo
6:05 pm - 6:10 pmGRR-MDW
1h 05mnonstop
Southwest Logo
9:30 am - 11:25 amMDW-GRR
0h 55mnonstop
$97Southwest
Find Deal
Mo, Okt 13 - Mo, Okt 20
United Airlines Logo
7:30 am - 7:41 amGRR-ORD
1h 11mnonstop
United Airlines Logo
8:45 am - 10:46 amORD-GRR
1h 01mnonstop
$97United Airlines
Find Deal
Do, Okt 9 - Mo, Okt 13
American Airlines Logo
5:33 pm - 5:44 pmGRR-ORD
1h 11mnonstop
American Airlines Logo
9:40 pm - 11:45 pmORD-GRR
1h 05mnonstop
$98American Airlines
Find Deal
Fr, Okt 10 - Mo, Okt 13
American Airlines Logo
6:00 am - 6:05 amGRR-ORD
1h 05mnonstop
American Airlines Logo
9:40 pm - 11:45 pmORD-GRR
1h 05mnonstop
$134American Airlines
Find Deal
Di, Feb 24 - Sa, Feb 28
United Airlines Logo
9:00 am - 9:12 amGRR-ORD
1h 12mnonstop
United Airlines Logo
10:35 am - 12:45 pmORD-GRR
1h 10mnonstop
$157United Airlines
Find Deal
Do, Okt 2 - Fr, Okt 3
Frontier Logo
4:20 pm - 11:59 pmGRR-ORD
8h 39m1 stop
Frontier Logo
10:42 am - 7:38 pmORD-GRR
7h 56m1 stop
$161Frontier
Find Deal
Mi, Okt 22 - Sa, Okt 25
Southwest Logo
3:55 pm - 8:50 pmGRR-MDW
5h 55m1 stop
Southwest Logo
9:55 am - 11:45 amMDW-GRR
0h 50mnonstop
$176Southwest
Find Deal
Do, Okt 2 - Do, Okt 9
Frontier Logo
1:22 pm - 7:44 pmGRR-ORD
7h 22m1 stop
Frontier Logo
5:05 am - 11:20 amORD-GRR
5h 15m1 stop
$177Frontier
Find Deal
Di, Feb 24 - Sa, Feb 28
Delta Logo
4:00 pm - 8:38 pmGRR-ORD
5h 38m1 stop
Delta Logo
10:35 am - 11:09 pmORD-GRR
11h 34m2 stops
$182Delta
Find Deal
Sa, Nov 1 - Di, Nov 4
Delta Logo
2:06 pm - 5:55 pmGRR-MDW
4h 49m1 stop
Delta Logo
9:35 am - 3:29 pmMDW-GRR
4h 54m1 stop
$208Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
United's Economy Plus offers extra legroom on this route.
Southwest's EarlyBird Check-In helps avoid middle seats.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Southwest
Cheapest • from $97 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Video guide: How to find cheap flights to Chicago
Watch video
Watch video
Watch video
Watch video
Top routes
GRR-MDW
Cheapest • 4% average savings
GRR-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 57% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 55% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$97
Southwest
Do 10/9Mo 10/13
GRR - MDW • Non-stop
Cheapest one-way
$49
Southwest
Do 10/16
GRR - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Expert advice

Expert advice for your flight from Grand Rapids to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

American's Main Cabin Extra includes early boarding and complimentary drinks.


American Airlines offers free Wi-Fi for T-Mobile customers on most flights.

United Airlines

United offers Priority Boarding to avoid gate-checking your carry-on bag.


United's Economy Plus seats offer up to six inches more legroom than standard economy.

Southwest

Southwest offers free carry-on and personal item, but checked bags now incur fees.


Southwest's cancellation policy allows changes up to 10 minutes before departure.

Read more about Southwestby Blane Bachelor
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Booking Insights

KAYAK's insights & trends for Grand Rapids to Chicago flights

Get data-powered insights and trends into flights from Grand Rapids to Chicago to help you find the cheapest flights, the best time to fly and much more.

Find cheap flights to Chicago
Find cheap flights to Chicago

Planning a trip from Grand Rapids to Chicago? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

How much is a round-trip flight from Grand Rapids to Chicago?

What is the cheapest Grand Rapids to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Grand Rapids to Chicago costs $215 on the route between Grand Rapids (GRR) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 4% cheaper than other Grand Rapids-Chicago routes. The most popular route is between Grand Rapids (GRR) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Grand Rapids to Chicago?

The average price of all round-trip flights from Grand Rapids to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Grand Rapids to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Mondays for the best deals.

What is the cheapest month to fly from Grand Rapids to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Grand Rapids to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Grand Rapids to Chicago is October, where tickets cost $132 (return) on average. On the other hand, the most expensive months are February and June, where the average cost of round-trip tickets is $519 and $373 respectively.

Can I save money by flying with a layover from Grand Rapids to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $155, prices are generally cheapest when you fly direct.

How far in advance should I book a flight from Grand Rapids to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Grand Rapids to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Grand Rapids to Chicago, you should book around 4 weeks before departure, which saves you about 57% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonJuly
Cheapest flight$49
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly with an average 5% increase in price.
Flight from Grand Rapids to Chicago Midway Airport

When to book flights from Grand Rapids to Chicago

Are your dates flexible? Find out the best times to travel from Grand Rapids to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Grand Rapids to Chicago

  • How does American Airlines support sustainable travel on flights from Grand Rapids to Chicago?

    American Airlines supports sustainable travel on flights from Grand Rapids to Chicago by implementing various initiatives. They prioritize fuel efficiency, utilize advanced aircraft technology, and implement sustainable practices in their operations. They also promote carbon offset programs and invest in renewable energy projects to minimize their environmental impact. Through these measures, American Airlines aims to reduce emissions and promote sustainable travel options for passengers on this route.

  • What are the in-flight entertainment amenities available on American Airlines flights from Grand Rapids to Chicago?

    American Airlines offers a range of in-flight entertainment amenities on flights from Grand Rapids to Chicago. Passengers can enjoy a variety of movies, TV shows, and music through the seat back screens or personal devices using the airline's entertainment system. Additionally, Wi-Fi is available for internet access, and power outlets are provided to keep devices charged.

  • Can I rent a car after my flight from Grand Rapids to Chicago?

    You can rent a car after your flight from Grand Rapids to Chicago. There are several rental companies available at Chicago's airports, including O'Hare International Airport and Midway International Airport. Some popular rental companies in the area include Hertz, Enterprise, Avis, Budget, and National Car Rental. You can easily find their counters and book a car upon arrival at the airport.

  • Can I pre-select my seat when flying American Airlines from Grand Rapids to Chicago?

    American Airlines generally allows passengers to pre-select their seats when flying from Grand Rapids to Chicago. During the booking process or after purchasing your ticket, you should have the option to choose your preferred seat. You can either select a specific seat or let the system assign one for you.

  • What is the cheapest flight from Grand Rapids to Chicago?

    In the last 3 days, the lowest price for a flight from Grand Rapids to Chicago was $49 for a one-way ticket and $97 for a round-trip.

  • Do I need a passport to fly between Grand Rapids and Chicago?

    A passport is not required to fly from Grand Rapids to Chicago.

  • Which airlines offer Wi-Fi service onboard planes from Grand Rapids to Chicago?

    American Airlines, and Delta offer inflight Wi-Fi service on the Grand Rapids to Chicago flight route.

  • Which aircraft models fly most regularly from Grand Rapids to Chicago?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Grand Rapids to Chicago flight route.

  • Which airline alliances offer flights from Grand Rapids to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Grand Rapids and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Grand Rapids to Chicago?

    There are nonstop flights from Grand Rapids to Chicago on a daily basis.

  • Which is the best airline for flights from Grand Rapids to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Grand Rapids to Chicago are Southwest and United Airlines. With an average price for the route of $234 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $278 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Grand Rapids to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Grand Rapids to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Grand Rapids to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Grand Rapids is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Grand Rapids to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Grand Rapids with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Grand Rapids to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Grand Rapids up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Grand Rapids to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $166 or less one-way and $319 or less round-trip.
  • American Airlines offers a range of in-flight entertainment amenities on flights from Grand Rapids (GRR) to Chicago (CHI). Passengers can enjoy a variety of movies, TV shows, and music channels on seat back screens or personal devices through the airline's entertainment app. Additionally, Wi-Fi connectivity is available for browsing the internet or streaming content. Complimentary headphones are provided for enhanced audio experience.
  • Delta Air Lines operates flights from Grand Rapids to Chicago and provides access to their Delta Sky Club lounge for eligible passengers. The Delta Sky Club at Gerald R. Ford International Airport in Grand Rapids offers travelers a comfortable and convenient space to relax before their flight. Passengers can enjoy a serene atmosphere here while awaiting their departure to Chicago.
  • American Airlines supports sustainable travel on flights from Grand Rapids to Chicago by implementing various measures. They optimize flight routes, reduce fuel consumption, and employ modern aircraft with improved fuel efficiency. The airline also encourages recycling onboard, minimizes waste production, and promotes responsible resource management. These initiatives aim to reduce the environmental impact of air travel and contribute to a more sustainable aviation industry.
  • When flying American Airlines from Grand Rapids to Chicago, you can pre-select your seat. American Airlines allows passengers to choose their seats during the booking process or later through the Manage Reservations section on their website or mobile app. By providing your preferences, you can select a specific seat that suits your needs and preferences for the flight.
  • Frontier Airlines permits small pets in the cabin for flights from Grand Rapids to Chicago. The maximum weight allowed is 40 lbs, including the pet carrier. The pet carrier must fit under the seat in front of you, and a fee applies for bringing pets onboard.

Prefer to fly direct from Grand Rapids to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Grand Rapids Gerald R. Ford Intl to Chicago.
Find which airlines fly direct from Grand Rapids Gerald R. Ford Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Grand Rapids Gerald R. Ford Intl to Chicago

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Direct returns

Chicago to Grand Rapids Gerald R. Ford Intl

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Sunday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

See more direct flights

Reviews of the top 3 airlines serving from Grand Rapids to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Grand Rapids to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Grand Rapids to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4242 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Everything you need to know for your flight from Grand Rapids to Chicago

Information on your arrival and departure airports

Compare transportation modes for Grand Rapids to Chicago

Transportation modeAverage priceAverage duration
Flights$5531h 05m
Trains$824h 10m

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