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Cheap flights from Grand Rapids to Chicago from $39

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 9/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

United Airlines Logo
9:30 am - 9:41 amGRR-ORD
1h 11mnonstop
United Airlines Logo
8:45 am - 10:46 amORD-GRR
1h 01mnonstop
$97United Airlines
Find Deal
Wed, Sep 24 - Sat, Sep 27
American Airlines Logo
8:01 am - 8:25 amGRR-ORD
1h 24mnonstop
American Airlines Logo
2:03 pm - 4:14 pmORD-GRR
1h 11mnonstop
$104American Airlines
Find Deal
Mon, Nov 3 - Tue, Nov 18
Southwest Logo
5:00 pm - 5:05 pmGRR-MDW
1h 05mnonstop
Southwest Logo
9:30 am - 11:25 amMDW-GRR
0h 55mnonstop
$114Southwest
Find Deal
Tue, Oct 14 - Fri, Oct 17
Southwest Logo
7:00 am - 7:00 amGRR-MDW
1h 00mnonstop
Southwest Logo
9:45 am - 11:40 amMDW-GRR
0h 55mnonstop
$117Southwest
Find Deal
Sat, Sep 13 - Sat, Sep 20
American Airlines Logo
3:47 pm - 4:00 pmGRR-ORD
1h 13mnonstop
American Airlines Logo
10:05 pm - 11:59 pmORD-GRR
0h 54mnonstop
$117American Airlines
Find Deal
Sat, Oct 4 - Mon, Nov 3
United Airlines Logo
6:39 pm - 6:50 pmGRR-ORD
1h 11mnonstop
United Airlines Logo
6:05 pm - 8:14 pmORD-GRR
1h 09mnonstop
$137United Airlines
Find Deal
Mon, Sep 15 - Mon, Sep 22
Frontier Logo
1:22 pm - 7:44 pmGRR-ORD
7h 22m1 stop
Frontier Logo
6:00 am - 7:38 pmORD-GRR
12h 38m1 stop
$166Frontier
Find Deal
Thu, Sep 4 - Sun, Sep 7
Frontier Logo
1:22 pm - 7:44 pmGRR-ORD
7h 22m1 stop
Frontier Logo
6:00 am - 7:38 pmORD-GRR
12h 38m1 stop
$168Frontier
Find Deal
Thu, Sep 11 - Mon, Sep 15
Delta Logo
2:06 pm - 6:25 pmGRR-MDW
5h 19m1 stop
Delta Logo
9:30 am - 1:36 pmMDW-GRR
3h 06m1 stop
$177Delta
Find Deal
Mon, Nov 3 - Tue, Nov 18
Delta Logo
5:30 am - 9:23 amGRR-ORD
4h 53m1 stop
Delta Logo
1:25 pm - 5:31 pmORD-GRR
3h 06m1 stop
$177Delta
Find Deal
Wed, Oct 29 - Sat, Nov 1

United Airlines flights from Grand Rapids to Chicago

Our best United Airlines deals on Grand Rapids to Chicago flight tickets
United Airlines
Sep 24
GRR9:30 amGrand Rapids Gerald R. Ford Intl
1h 11m
ORD9:41 amChicago O'Hare Intl
Sep 27
ORD8:45 amChicago O'Hare Intl
1h 01m
GRR10:46 amGrand Rapids Gerald R. Ford Intl
$97
Find similar
United Airlines
Sep 15
GRR6:39 pmGrand Rapids Gerald R. Ford Intl
1h 11m
ORD6:50 pmChicago O'Hare Intl
Sep 22
ORD6:05 pmChicago O'Hare Intl
1h 09m
GRR8:14 pmGrand Rapids Gerald R. Ford Intl
$137
Find similar
United Airlines
Sep 11
GRR3:44 pmGrand Rapids Gerald R. Ford Intl
1h 16m
ORD4:00 pmChicago O'Hare Intl
Sep 15
ORD9:35 pmChicago O'Hare Intl
1h 07m
GRR11:42 pmGrand Rapids Gerald R. Ford Intl
$174
Find similar

American Airlines flights from Grand Rapids to Chicago

Our best American Airlines deals on Grand Rapids to Chicago flight tickets
American Airlines
Nov 3
GRR8:01 amGrand Rapids Gerald R. Ford Intl
1h 24m
ORD8:25 amChicago O'Hare Intl
Nov 18
ORD2:03 pmChicago O'Hare Intl
1h 11m
GRR4:14 pmGrand Rapids Gerald R. Ford Intl
$104
Find similar
American Airlines
Oct 4
GRR3:47 pmGrand Rapids Gerald R. Ford Intl
1h 13m
ORD4:00 pmChicago O'Hare Intl
Nov 3
ORD10:05 pmChicago O'Hare Intl
0h 54m
GRR11:59 pmGrand Rapids Gerald R. Ford Intl
$117
Find similar
American Airlines
Sep 11
GRR7:32 pmGrand Rapids Gerald R. Ford Intl
1h 14m
ORD7:46 pmChicago O'Hare Intl
Sep 15
ORD7:10 amChicago O'Hare Intl
0h 59m
GRR9:09 amGrand Rapids Gerald R. Ford Intl
$118
Find similar

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 17, 2025.
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

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Wed 9/24

9:30 am-9:41 am

Nonstop1h 11m

Chicago O'Hare Intl

Sat 9/27

8:45 am-10:46 am

Nonstop1h 01m

$97

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Mon 11/3

8:01 am-8:25 am

Nonstop1h 24m

Chicago O'Hare Intl

Tue 11/18

2:03 pm-4:14 pm

Nonstop1h 11m

$104

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Tue 10/14

5:00 pm-5:05 pm

Nonstop1h 05m

Chicago Midway

Fri 10/17

9:30 am-11:25 am

Nonstop0h 55m

$114

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Sat 9/13

7:00 am-7:00 am

Nonstop1h 00m

Chicago Midway

Sat 9/20

9:45 am-11:40 am

Nonstop0h 55m

$117

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Sat 10/4

3:47 pm-4:00 pm

Nonstop1h 13m

Chicago O'Hare Intl

Mon 11/3

10:05 pm-11:59 pm

Nonstop0h 54m

$117

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Mon 9/15

6:39 pm-6:50 pm

Nonstop1h 11m

Chicago O'Hare Intl

Mon 9/22

6:05 pm-8:14 pm

Nonstop1h 09m

$137

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Thu 9/4

1:22 pm-7:44 pm

1 stop7h 22m

Chicago O'Hare Intl

Sun 9/7

6:00 am-7:38 pm

1 stop12h 38m

$166

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Thu 9/11

1:22 pm-7:44 pm

1 stop7h 22m

Chicago O'Hare Intl

Mon 9/15

6:00 am-7:38 pm

1 stop12h 38m

$168

Grand RapidsChicago

GRR - MDW

GRRMDW

Grand Rapids Gerald R. Ford Intl

Mon 11/3

2:06 pm-6:25 pm

1 stop5h 19m

Chicago Midway

Tue 11/18

9:30 am-1:36 pm

1 stop3h 06m

$177

Grand RapidsChicago

GRR - ORD

GRRORD

Grand Rapids Gerald R. Ford Intl

Wed 10/29

5:30 am-9:23 am

1 stop4h 53m

Chicago O'Hare Intl

Sat 11/1

1:25 pm-5:31 pm

1 stop3h 06m

$177

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 October is, on average, the cheapest month to fly to Chicago from Grand Rapids, with most prices found around $159. If you’re not able to fly to Chicago in October, then August is your next best option. Flight prices from Grand Rapids to Chicago during August average around $211.

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 Thursday when prices can be found for as low as $492. 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 $572.

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 $498. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $678.

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

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

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

You are more likely to see cheaper flights to Chicago from Grand Rapids when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $259 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Grand Rapids for as low as $161 on momondo.

What cabin class options are available on Grand Rapids Gerald R. Ford Intl to Chicago flights?

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

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

As of August 2025, prices for Grand Rapids to Chicago flights are approximately 30% cheaper 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

$39

Fastest flight time

0h 55m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Grand Rapids in the past 72 hours is $39. The best round-trip flight deal from Grand Rapids to Chicago found on momondo in the last 72 hours is $97.
The fastest flight from Grand Rapids to Chicago takes 0h 55m
Direct flights go from Grand Rapids to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • 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 0h 55m.

  • 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 $97Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $122Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
United AirlinesPriceFrom $132Free CancellationRating
7.4
8,919 reviews
Search United Airlines flights

  • Southwest Flights From Grand Rapids to Chicago

    Across 14 Southwest flights from Grand Rapids to Chicago this week, the average price was $275, with the best Southwest deals starting from $122 round-trip. 4,246 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 8,919 reviews) operates around 21 flights from Grand Rapids to Chicago in any given week. The average United Airlines airfare for this route is around $273, with deals from around $132 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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