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Cheap flights from Grand Rapids to Chicago from $66

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Grand Rapids to Chicago departing on 9/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Grand Rapids to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:30 am - 6:40 amGRR  Grand Rapids Gerald R. Ford Intl-MDW Chicago Midway
1h 10mnonstop
Southwest Logo
4:00 pm - 5:50 pmMDW  Chicago Midway-GRR Grand Rapids Gerald R. Ford Intl
0h 50mnonstop
$145Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
6:45 am - 6:45 amGRR  Grand Rapids Gerald R. Ford Intl-MDW Chicago Midway
1h 00mnonstop
Southwest Logo
9:40 am - 11:35 amMDW  Chicago Midway-GRR Grand Rapids Gerald R. Ford Intl
0h 55mnonstop
$154Southwest
Thu, Oct 29 - Fri, Oct 30
Southwest Logo
2:15 pm - 8:35 pmGRR  Grand Rapids Gerald R. Ford Intl-MDW Chicago Midway
7h 20m1 stop Baltimore/Washington
Southwest Logo
11:15 am - 1:05 pmMDW  Chicago Midway-GRR Grand Rapids Gerald R. Ford Intl
0h 50mnonstop
$154Southwest
Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
7:23 am - 8:01 amGRR  Grand Rapids Gerald R. Ford Intl-ORD Chicago O'Hare Intl
1h 38mnonstop
American Airlines Logo
11:46 am - 1:51 pmORD  Chicago O'Hare Intl-GRR Grand Rapids Gerald R. Ford Intl
1h 05mnonstop
$157American Airlines
Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
7:23 am - 8:01 amGRR  Grand Rapids Gerald R. Ford Intl-ORD Chicago O'Hare Intl
1h 38mnonstop
American Airlines Logo
11:46 am - 1:51 pmORD  Chicago O'Hare Intl-GRR Grand Rapids Gerald R. Ford Intl
1h 05mnonstop
$158American Airlines
Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
9:38 am - 10:08 amGRR  Grand Rapids Gerald R. Ford Intl-ORD Chicago O'Hare Intl
1h 30mnonstop
American Airlines Logo
10:40 pm - 12:51 amORD  Chicago O'Hare Intl-GRR Grand Rapids Gerald R. Ford Intl
1h 11mnonstop
$166American Airlines
Thu, Oct 29 - Fri, Oct 30
United Airlines Logo
11:07 am - 11:29 amGRR  Grand Rapids Gerald R. Ford Intl-ORD Chicago O'Hare Intl
1h 22mnonstop
United Airlines Logo
7:50 pm - 9:57 pmORD  Chicago O'Hare Intl-GRR Grand Rapids Gerald R. Ford Intl
1h 07mnonstop
$175United Airlines
Wed, Oct 28 - Wed, Nov 11
United Airlines Logo
5:00 am - 5:15 amGRR  Grand Rapids Gerald R. Ford Intl-ORD Chicago O'Hare Intl
1h 15mnonstop
United Airlines Logo
7:59 pm - 10:06 pmORD  Chicago O'Hare Intl-GRR Grand Rapids Gerald R. Ford Intl
1h 07mnonstop
$175United Airlines
Wed, Sep 16 - Wed, Sep 16
Delta Logo
5:30 am - 9:07 amGRR  Grand Rapids Gerald R. Ford Intl-MDW Chicago Midway
4h 37m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 1:58 pmMDW  Chicago Midway-GRR Grand Rapids Gerald R. Ford Intl
3h 29m1 stop Detroit Metropolitan Wayne County
$195Delta
Wed, Sep 9 - Thu, Sep 10
Delta Logo
5:30 am - 9:17 amGRR  Grand Rapids Gerald R. Ford Intl-MDW Chicago Midway
4h 47m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:24 am - 1:53 pmMDW  Chicago Midway-GRR Grand Rapids Gerald R. Ford Intl
3h 29m1 stop Detroit Metropolitan Wayne County
$195Delta
Wed, Sep 2 - Thu, Sep 3

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Delta flights from Grand Rapids to Chicago

Our best Delta deals on Grand Rapids to Chicago flight tickets
Delta
Oct 12
GRR6:02 pmGrand Rapids Gerald R. Ford Intl
3h 28m
1 stop
ORD8:30 pmChicago O'Hare Intl
Oct 27
ORD7:10 amChicago O'Hare Intl
5h 13m
1 stop
GRR1:23 pmGrand Rapids Gerald R. Ford Intl
$195
Delta
Oct 16
GRR3:47 pmGrand Rapids Gerald R. Ford Intl
5h 43m
1 stop
ORD8:30 pmChicago O'Hare Intl
Oct 22
ORD1:55 pmChicago O'Hare Intl
4h 02m
1 stop
GRR6:57 pmGrand Rapids Gerald R. Ford Intl
$219
Delta
Oct 16
GRR3:47 pmGrand Rapids Gerald R. Ford Intl
5h 43m
1 stop
ORD8:30 pmChicago O'Hare Intl
Oct 23
ORD11:19 amChicago O'Hare Intl
4h 44m
1 stop
GRR5:03 pmGrand Rapids Gerald R. Ford Intl
$243

American Airlines flights from Grand Rapids to Chicago

Our best American Airlines deals on Grand Rapids to Chicago flight tickets
American Airlines
Sep 5
GRR7:23 amGrand Rapids Gerald R. Ford Intl
1h 38m
ORD8:01 amChicago O'Hare Intl
Sep 6
ORD11:46 amChicago O'Hare Intl
1h 05m
GRR1:51 pmGrand Rapids Gerald R. Ford Intl
$157
American Airlines
Sep 5
GRR7:23 amGrand Rapids Gerald R. Ford Intl
1h 38m
ORD8:01 amChicago O'Hare Intl
Sep 6
ORD11:46 amChicago O'Hare Intl
1h 05m
GRR1:51 pmGrand Rapids Gerald R. Ford Intl
$158
American Airlines
Oct 29
GRR9:38 amGrand Rapids Gerald R. Ford Intl
1h 30m
ORD10:08 amChicago O'Hare Intl
Oct 30
ORD10:40 pmChicago O'Hare Intl
1h 11m
GRR12:51 amGrand Rapids Gerald R. Ford Intl
$166

momondo Fare Finder

 
Customize your flight search to find flights from Grand Rapids to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 12, 2026.
Use the filters below to find and compare flights from Grand Rapids to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 9/5

6:30 am-6:40 am

Nonstop1h 10m

Chicago Midway

Sun 9/6

4:00 pm-5:50 pm

Nonstop0h 50m

$145
Quickest round-trip

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway

GRRMDW

Grand Rapids Gerald R. Ford Intl

Thu 10/29

6:45 am-6:45 am

Nonstop1h 00m

Chicago Midway

Fri 10/30

9:40 am-11:35 am

Nonstop0h 55m

$154

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 9/5

2:15 pm-8:35 pm

1 stop7h 20m

Chicago Midway

Sun 9/6

11:15 am-1:05 pm

Nonstop0h 50m

$154

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl

GRRORD

Grand Rapids Gerald R. Ford Intl

Sat 9/5

7:23 am-8:01 am

Nonstop1h 38m

Chicago O'Hare Intl

Sun 9/6

11:46 am-1:51 pm

Nonstop1h 05m

$157

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl

GRRORD

Grand Rapids Gerald R. Ford Intl

Sat 9/5

7:23 am-8:01 am

Nonstop1h 38m

Chicago O'Hare Intl

Sun 9/6

11:46 am-1:51 pm

Nonstop1h 05m

$158

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl

GRRORD

Grand Rapids Gerald R. Ford Intl

Thu 10/29

9:38 am-10:08 am

Nonstop1h 30m

Chicago O'Hare Intl

Fri 10/30

10:40 pm-12:51 am

Nonstop1h 11m

$166

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl

GRRORD

Grand Rapids Gerald R. Ford Intl

Wed 10/28

11:07 am-11:29 am

Nonstop1h 22m

Chicago O'Hare Intl

Wed 11/11

7:50 pm-9:57 pm

Nonstop1h 07m

$175

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - ORD Chicago O'Hare Intl

GRRORD

Grand Rapids Gerald R. Ford Intl

Wed 9/16

5:00 am-5:15 am

Nonstop1h 15m

Chicago O'Hare Intl

Wed 9/16

7:59 pm-10:06 pm

Nonstop1h 07m

$175

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 9/9

5:30 am-9:07 am

1 stop4h 37m

Chicago Midway

Thu 9/10

9:29 am-1:58 pm

1 stop3h 29m

$195

Grand RapidsChicago

GRR Grand Rapids Gerald R. Ford Intl - MDW Chicago Midway

GRRMDW

Grand Rapids Gerald R. Ford Intl

Wed 9/2

5:30 am-9:17 am

1 stop4h 47m

Chicago Midway

Thu 9/3

9:24 am-1:53 pm

1 stop3h 29m

$195

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Grand Rapids to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Grand Rapids, with most prices found around $177. If you’re not able to fly to Chicago in November, then September is your next best option. Flight prices from Grand Rapids to Chicago during September average around $204.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as $487. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Grand Rapids to Chicago for around $570.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Grand Rapids to Chicago during this time can be as low as $474. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $698.

What is the cheapest Grand Rapids Gerald R. Ford Intl to Chicago flight route?

Fly from Grand Rapids Gerald R. Ford Intl to Chicago O'Hare Intl for the best Grand Rapids Gerald R. Ford Intl - Chicago flight prices

What cabin class options are available on Grand Rapids to Chicago flights?

There are 4 cabin classes available to choose from on Grand Rapids to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Grand Rapids to Chicago flights?

No. A direct flight is the cheapest option for a flight between Grand Rapids to Chicago.

How have Grand Rapids to Chicago flight prices changed over time?

As of August 2026, prices for Grand Rapids to Chicago flights are approximately 117% more expensive when compared to flights at the same time last year.

When to book flights from Grand Rapids to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Grand Rapids to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Grand Rapids to Chicago (GRR to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Grand Rapids to Chicago

Best Price Found

$209

Fastest flight time

1h 00m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Grand Rapids in the past 72 hours is $209. The best round-trip flight deal from Grand Rapids to Chicago found on momondo in the last 72 hours is $358.
The fastest flight from Grand Rapids to Chicago takes 1h 00m
Direct flights go from Grand Rapids to Chicago every day.
There are 3 airports in Chicago. From Grand Rapids there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Grand Rapids to Chicago

  • How far is Grand Rapids Gerald R. Ford Intl to Chicago by plane?

    The distance between Grand Rapids Gerald R. Ford Intl and Chicago is about 125.0 mi. In terms of flight time, this usually takes a little over 1h 00m.

  • When did momondo last update prices for flights from Grand Rapids Gerald R. Ford Intl Airport to Chicago?

    Prices for flights from Grand Rapids Gerald R. Ford Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Grand Rapids Gerald R. Ford Intl Airport to Chicago?

  • How old do you have to be to fly from Grand Rapids Gerald R. Ford Intl Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Grand Rapids Gerald R. Ford Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Grand Rapids to Chicago?

  • What is the most popular airline from Grand Rapids to Chicago?

Best airlines flying from Grand Rapids to Chicago

Compare and see reviews for airlines that fly from Grand Rapids to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $91Free CancellationRating
7.1
11,917 reviews
Search American Airlines flights
SouthwestPriceFrom $97Free CancellationRating
8.0
4,220 reviews
Search Southwest flights
United AirlinesPriceFrom $114Free CancellationRating
7.4
10,112 reviews
Search United Airlines flights

  • Southwest Flights From Grand Rapids to Chicago

    Across 15 Southwest flights from Grand Rapids to Chicago this week, the average price was $302, with the best Southwest deals starting from $97 round-trip. 4,220 users have rated Southwest on momondo, with an average score of 8.0/10.

  • United Airlines Flights From Grand Rapids to Chicago

    United Airlines (7.4/10 from 10,112 reviews) operates around 16 flights from Grand Rapids to Chicago in any given week. The average United Airlines airfare for this route is around $279, with deals from around $114 rare but found on momondo. Referenced prices are for round-trip Grand Rapids to Chicago flight searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Grand Rapids to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Grand Rapids.

Can I find flights from Grand Rapids to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Grand Rapids on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Grand Rapids to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Grand Rapids. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Grand Rapids to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Grand Rapids. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport