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 12/3. 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, 0 bags

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

Thu, Dec 4 - Mon, Dec 8
Southwest Logo
5:00 pm - 5:15 pmGRR-MDW
1h 15mnonstop
Southwest Logo
8:40 pm - 10:35 pmMDW-GRR
0h 55mnonstop
$97Southwest
Find Deal
Tue, Dec 9 - Tue, Dec 16
American Airlines Logo
6:45 am - 7:06 amGRR-ORD
1h 21mnonstop
American Airlines Logo
9:40 am - 11:56 amORD-GRR
1h 16mnonstop
$97American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
American Airlines Logo
7:26 pm - 7:52 pmGRR-ORD
1h 26mnonstop
American Airlines Logo
6:57 am - 8:58 amORD-GRR
1h 01mnonstop
$99American Airlines
Find Deal
Thu, Dec 4 - Mon, Dec 8
Southwest Logo
5:00 pm - 5:15 pmGRR-MDW
1h 15mnonstop
Southwest Logo
6:40 am - 2:10 pmMDW-GRR
6h 30m1 stop
$107Southwest
Find Deal
Wed, Dec 3 - Thu, Dec 11
Delta Logo
3:37 pm - 8:35 pmGRR-ORD
5h 58m1 stop
Delta Logo
6:00 am - 10:53 amORD-GRR
3h 53m1 stop
$157Delta
Find Deal
Mon, Nov 24 - Mon, Nov 24
United Airlines Logo
6:12 am - 6:30 amGRR-ORD
1h 18mnonstop
United Airlines Logo
3:35 pm - 5:36 pmORD-GRR
1h 01mnonstop
$159United Airlines
Find Deal
Tue, Jan 13 - Sat, Jan 17
Delta Logo
8:10 am - 1:07 pmGRR-ORD
5h 57m1 stop
Delta Logo
11:05 am - 3:17 pmORD-GRR
3h 12m1 stop
$167Delta
Find Deal
Thu, Nov 27 - Thu, Dec 4
United Airlines Logo
7:30 am - 7:42 amGRR-ORD
1h 12mnonstop
United Airlines Logo
2:09 pm - 4:01 pmORD-GRR
0h 52mnonstop
$169United Airlines
Find Deal
Mon, Nov 10 - Thu, Nov 13
Frontier Logo
8:02 pm - 3:08 pmGRR-ORD
20h 06m1 stop
Frontier Logo
5:25 am - 6:33 pmORD-GRR
12h 08m1 stop
$265Frontier
Find Deal
Thu, Nov 13 - Mon, Nov 17
Frontier Logo
8:49 pm - 10:10 pmGRR-MDW
26h 21m2 stops
Frontier Logo
9:27 am - 7:07 pmMDW-GRR
8h 40m1 stop
$285Frontier
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 • 5% average savings
GRR-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
5 weeks
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 60% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
October
Cheapest • 39% price drop
November
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$97
Southwest
Thu 12/4Mon 12/8
GRR - MDW • Non-stop
Cheapest one-way
$49
Southwest
Wed 12/3
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!
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.

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 $231 on the route between Grand Rapids (GRR) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 5% 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, Monday is the most expensive day to fly from Grand Rapids to Chicago. For your return ticket, we recommend flying on a Tuesday 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 $176 (return) on average. On the other hand, the most expensive months are February and June, where the average cost of round-trip tickets is $482 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 $263, 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 5 weeks before departure, which saves you about 60% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

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
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.

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.

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
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
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
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

Good to know

Low seasonJuly
Cheapest flight$49
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 2% lower on average.
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 $250 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 $285 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 $188 or less one-way and $332 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 4241 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

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.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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.

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$8631h 10m
Trains$1034h 11m
Buses$3004h 00m

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