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Cheap Flights from Grand Rapids to Chicago

Browse current best options from Grand Rapids. Become a member to unlock all deals and get alerts when new deals appear.

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Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Grand Rapids to Chicago

Explore current cheapest deals departing from Grand Rapids to Chicago

Round trip

Sort by: Cheapest

July 15 - July 22

Cheapest

Earliest

GRR - Chicago

$177

$157

Round trip

October 14 - October 21

GRR - Chicago

$194

$176

Round trip

August 8 - August 11

GRR - Chicago

$182

$176

Round trip

August 15 - August 19

GRR - Chicago

$183

$176

Round trip

September 7 - September 8

GRR - Chicago

$169

$176

Round trip

December 1 - December 15

Best

GRR - Chicago

$312

$177

Round trip

October 15 - October 22

GRR - Chicago

$195

$194

Round trip

October 17 - October 24

GRR - Chicago

$195

$194

Round trip

August 13 - August 17

GRR - Chicago

$182

$195

Round trip

September 17 - September 21

GRR - Chicago

$171

$195

Round trip

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Route Intelligence — 486,190 Searches this Week

Insights for flights from Grand Rapids to Chicago

For travelers looking for cheap flights from Grand Rapids to Chicago, March stands out as the most economical month, with a median fare of just $132. This is followed by January, which offers a median fare of $140, and July, with a median of $158. These months present the best opportunities for finding lower prices on this route.

Fares for flights from Grand Rapids to Chicago typically range from $171–$290, with a median price of $223. Right now, current fares are near the typical level for this route. Only 1% of recent fares were classified as a good price, indicating that finding exceptional deals can be challenging, though new deals appear almost daily.

When flying from Grand Rapids to Chicago, almost all itineraries are non-stop, with direct flights from Grand Rapids to Chicago making up 81.6% of recent fares. For the remaining itineraries that do include connections, a typical journey involves 2 stopovers.

A typical journey from Grand Rapids to Chicago takes approximately 1h 26m, including any connections. This short duration reflects the close proximity of the two cities, making it a convenient route for travelers.

The route from Grand Rapids to Chicago covers a distance of 220 kilometers, classifying it as a short-haul flight. This short distance contributes to the quick travel time and the prevalence of direct flight options.

How much is a round trip from Grand Rapids to Chicago

Regular price: $143 - $341

Prices for flights from Grand Rapids to Chicago are currently within the regular range.

The regular price range for flights from Grand Rapids to Chicago is between $143 and $341. The current lowest deal is $157 on Kayak for travel from July 15 to July 22.

now $157

Low $143

High $341

The cheapest time to fly from Grand Rapids to Chicago

The cheapest month to fly from GRR to CHI is March, with a median price of $132. The most expensive month is February, with a median price of $408. Prices are generally lower from January to December.

March

Cheapest

Flights from $132

February

Most Expensive

Flights from $408

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Grand Rapids to Chicago

American Airlines

Last-minute flights going from Grand Rapids to Chicago

Wed, Jun 17

⌛ Last-Minute

GRR - Chicago

Grand Rapids (GRR) - Chicago (ORD)

$404

$402

One-way

Tue, Jun 23

⌛ Last-Minute

GRR - Chicago

Grand Rapids (GRR) - Chicago (ORD)

United Airlines

$180

$328

One-way

Tue, Jun 30

⌛ Last-Minute

GRR - Chicago

Grand Rapids (GRR) - Chicago (ORD)

United Airlines

$163

$316

One-way

Tue, Jun 30

⌛ Last-Minute

GRR - Chicago

Grand Rapids (GRR) - Chicago (ORD)

United Airlines

$161

$316

One-way

Tue, Jun 30

⌛ Last-Minute

GRR - Chicago

Grand Rapids (GRR) - Chicago (ORD)

$303

$335

One-way

Wed, Jul 1

⌛ Last-Minute

GRR - Chicago

Grand Rapids (GRR) - Chicago (MDW)

Southwest Airlines

$152

$300

One-way

Biggest price drops on these dates for flights from Grand Rapids to Chicago

14 nights

Dec 1 - Dec 15

$312 → $177

43%

4 nights

Aug 6 - Aug 10

$341 → $214

37%

4 nights

Aug 6 - Aug 10

$329 → $215

35%

3 nights

Aug 17 - Aug 20

$327 → $220

33%

Popular Airports to fly from Grand Rapids to Chicago

Grand Rapids - Chicago route insights

💸 Price insights

Recent fares are near the typical level

Recent fares for Grand Rapids to Chicago are near the typical level of $223.

📅 Best time to fly

March is historically the cheapest month to fly

Historically, March is the cheapest month to fly from Grand Rapids to Chicago, with a median price of $132.

⏱️ Flight duration

Direct flights take 1h 26m

The typical direct flight from Grand Rapids to Chicago takes 1 hour and 26 minutes.

✈️ Airlines & availability

Direct flights are dominant on this route

Direct flights make up 81.6% of all deals from Grand Rapids to Chicago.

🏆 Airline highlight

American Airlines offers direct flights

American Airlines is an option for direct flights from Grand Rapids to Chicago.

🎯 Booking tip

Deals are frequent for this route

Deals for flights from Grand Rapids to Chicago are frequent, with over 1 deal per day.

Grand Rapids main airports to depart from

Gerald R. Ford International (GRR)

Cheapest

Gerald R. Ford International Airport is a good option for flights from Grand Rapids to Chicago.

📍 ~15 km from city center (reachable by car)

💸 Flights from ~$157

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a good option for flights from Grand Rapids to Chicago.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$157

Chicago Midway International (MDW)

Chicago Midway International Airport is another choice for your trip from Grand Rapids to Chicago.

📍 ~15 km from Chicago city center (reachable by car)

💸 Flights from ~$176

Chicago Rockford International (RFD)

Consider Chicago Rockford International Airport for your arrival when flying from Grand Rapids to Chicago.

📍 ~120 km from Chicago city center (reachable by car)

💸 Flights from ~$229

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International Airport is a useful alternative with high-frequency flight options to Chicago.

📍 ~135 km from Chicago (reachable by car or Amtrak Hiawatha service)

💸 Flights from ~$273

South Bend International (SBN)

Cheapest

South Bend International Airport is a useful alternative, geographically closest to the Chicago area.

📍 ~120 km from Chicago (reachable by car or South Shore Line commuter rail)

💸 Flights from ~$225

Dane County Regional (MSN)

Dane County Regional Airport is a reliable regional alternative for those seeking less congestion than Chicago.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$290

Fort Wayne International (FWA)

Fort Wayne International Airport offers stable regional service for travelers in southeastern Chicago suburbs.

📍 ~230 km from Chicago (reachable by car)

💸 Flights from ~$278

Business & First Class Flight Deals to Chicago

41% AI deal score

$514

From GRR

Elite

Sep 02

Chicago, United States

40% AI deal score

$435

$418

Save $17

From GRR

Elite

Sep 06

Chicago, United States

40% AI deal score

$455

$436

Save $19

From GRR

Elite

Sep 06

Chicago, United States

39% AI deal score

$450

$436

Save $14

From GRR

Elite

Sep 07

Chicago, United States

39% AI deal score

$449

$437

Save $12

From GRR

Elite

Sep 02

Chicago, United States

38% AI deal score

$436

From GRR

Elite

Sep 08

Chicago, United States

38% AI deal score

Chicago, United States

32% AI deal score

$984

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Grand Rapids to Chicago is typically 14-27 days before departure. During this period, the average price observed was $205. Booking within 0-6 days of departure generally sees a higher average price of $283. For those booking 7-13 days out, the average price was $295.

Across the trailing quarter, a flight from Grand Rapids to Chicago is considered a good deal if it is priced at or below $171. The median price for this route over the same period was $223. Prices at the 75th percentile reached $290, indicating higher costs for a significant portion of bookings.

Historically, March has been the cheapest month to fly from Grand Rapids to Chicago, with a median price of $132. January also offers competitive prices, with a median of $140. While July is listed as the most expensive month, its median price of $158 is still relatively low compared to the annual median of $223 for this route.

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