Search Cheap Flights to
Des Plaines

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Des Plaines Flights as Low as $205

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Tue, Oct 20 - Tue, Oct 27
BOS
Logan Intl.
ORD
O'Hare Intl.
$205 Roundtrip, found 6 hours ago
$205
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Tue, Oct 20 from Logan Intl. to O'Hare Intl., returning Tue, Oct 27, priced at $205 found 6 hours ago
Bargain Flight
Wed, Nov 11 - Wed, Nov 11
BOS
Logan Intl.
ORD
O'Hare Intl.
$206 Roundtrip, found 5 hours ago
$206
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Wed, Nov 11 from Logan Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $206 found 5 hours ago
Delta
Tue, Oct 20 - Tue, Oct 27
BOS
Logan Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 6 hours ago
$209
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Oct 20 from Logan Intl. to O'Hare Intl., returning Tue, Oct 27, priced at $209 found 6 hours ago
JetBlue Airways
Tue, Oct 20 - Tue, Oct 27
BOS
Logan Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 6 hours ago
$209
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Tue, Oct 20 from Logan Intl. to O'Hare Intl., returning Tue, Oct 27, priced at $209 found 6 hours ago
Bargain Flight
Tue, Oct 20 - Thu, Oct 29
BOS
Logan Intl.
ORD
O'Hare Intl.
$211 Roundtrip, found 6 hours ago
$211
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Tue, Oct 20 from Logan Intl. to O'Hare Intl., returning Thu, Oct 29, priced at $211 found 6 hours ago
JetBlue Airways
Tue, Nov 10 - Tue, Nov 17
BOS
Logan Intl.
ORD
O'Hare Intl.
$212 Roundtrip, found 2 hours ago
$212
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Nov 10 from Logan Intl. to O'Hare Intl., returning Tue, Nov 17, priced at $212 found 2 hours ago
Bargain Flight
Tue, Nov 10 - Mon, Nov 16
BOS
Logan Intl.
ORD
O'Hare Intl.
$215 Roundtrip, found 5 hours ago
$215
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Tue, Nov 10 from Logan Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $215 found 5 hours ago
United
Tue, Oct 20 - Tue, Oct 27
BOS
Logan Intl.
ORD
O'Hare Intl.
$219 Roundtrip, found 6 hours ago
$219
Roundtrip
found 6 hours ago
Select United flight, departing Tue, Oct 20 from Logan Intl. to O'Hare Intl., returning Tue, Oct 27, priced at $219 found 6 hours ago
Bargain Flight
Thu, Nov 12 - Mon, Nov 16
BOS
Logan Intl.
ORD
O'Hare Intl.
$221 Roundtrip, found 2 hours ago
$221
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Thu, Nov 12 from Logan Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $221 found 2 hours ago
Bargain Flight
Sat, Dec 5 - Tue, Dec 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$222 Roundtrip, found 5 hours ago
$222
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Sat, Dec 5 from Logan Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $222 found 5 hours ago
Bargain Flight
Thu, Nov 26 - Fri, Nov 27
BOS
Logan Intl.
ORD
O'Hare Intl.
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Nov 26 from Logan Intl. to O'Hare Intl., returning Fri, Nov 27, priced at $224 found 1 day ago
Southwest Airlines
Tue, Nov 10 - Sat, Nov 14
BOS
Logan Intl.
MDW
Midway Intl.
$225 Roundtrip, just found
$225
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Nov 10 from Logan Intl. to Midway Intl., returning Sat, Nov 14, priced at $225 just found
JetBlue Airways
Tue, Nov 10 - Mon, Nov 16
BOS
Logan Intl.
ORD
O'Hare Intl.
$225 Roundtrip, found 2 hours ago
$225
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Nov 10 from Logan Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $225 found 2 hours ago
American Airlines
Thu, Nov 12 - Mon, Nov 16
BOS
Logan Intl.
ORD
O'Hare Intl.
$239 Roundtrip, found 2 hours ago
$239
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Nov 12 from Logan Intl. to O'Hare Intl., returning Mon, Nov 16, priced at $239 found 2 hours ago
Frontier Airlines
Sun, Nov 22 - Fri, Dec 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Nov 22 from Logan Intl. to O'Hare Intl., returning Fri, Dec 4, priced at $250 found 1 day ago
American Airlines
Tue, Sep 29 - Thu, Oct 1
BOS
Logan Intl.
RFD
Greater Rockford
$380 Roundtrip, found 1 hour ago
$380
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Sep 29 from Logan Intl. to Greater Rockford, returning Thu, Oct 1, priced at $380 found 1 hour ago

Cheap Flights to Des Plaines

Fall in love at first flight with your vacation to Des Plaines by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Des Plaines on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Des Plaines, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Des Plaines

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Des Plaines with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Des Plaines?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Des Plaines are in October, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Des Plaines?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 9 to choose from for your flight to Des Plaines.

What airport is best to fly into Des Plaines?

When you’re planning your trip to Des Plaines, convenience is the name of the game. Luckily, Des Plaines O'Hare Intl. Airport is nearby so you can deplane and get going on checking off everything on your Des Plaines must-do list.

How much are flights to Des Plaines?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Des Plaines on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $205, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Des Plaines?

The trick to saving a stack of cash on your flight to Des Plaines? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $205 right now, why wait?

Des Plaines Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$148

Last Minute Hotel Deals in Des Plaines

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
3001 South Mannheim Road Des Plaines IL
Book a stay at this business-friendly hotel in Des Plaines. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
8.8/10 Excellent! (2,043 reviews)
"The stay was ok but we didn’t have towels they kept saying they were out our room had 1 face towel and two bath-towels it was 3 of us in the room. The morning of check out we still had to go down and ask for towels twice. The lights were out in the door way they never replaced the bulb. And there ..."

Reviewed on Sep 27, 2026

Get rates
Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,458 reviews)
"Our room was so small and had no windows that could get any light. For the cost I just felt ripped off."

Reviewed on Sep 28, 2026

Get rates
River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Get rates
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,372 reviews)
"We chose this hotel to celebrate the 10th anniversary of the day we met, and we were really looking forward to a pleasant evening. We arrived late in the evening and were given a room that had not been cleaned. The bed was unmade, so we went to the front desk and asked for another room. We were told ..."

Reviewed on Sep 28, 2026

Get rates
The Chicago Hotel Collection Ambassador Gold Coast
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
Get rates
Hampton Inn Chicago Downtown/Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (2,256 reviews)
"We had a nice room. It was clean. Wasn't impressed with the bedding or the cleanliness of the common areas. Location was great though and we had a reasonable rate."

Reviewed on Sep 28, 2026

Get rates
The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
Get rates
Hilton Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (2,678 reviews)
"The staff was amazing."

Reviewed on Sep 27, 2026

Get rates
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
See all 4,892 properties in Des Plaines
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Hotels With Free Airport Shuttle

Wyndham Chicago O'Hare

Wyndham Chicago O'Hare

3 out of 5
1450 E Touhy Ave Des Plaines IL
Book a stay at this business-friendly hotel in Des Plaines. Enjoy breakfast (surcharge), a free airport shuttle, and a 24-hour fitness center. Our guests praise ...
Get rates
Wyndham Chicago O'Hare
Spark by Hilton Des Plaines Chicago O'Hare

Spark by Hilton Des Plaines Chicago O'Hare

3 out of 5
2175 E Touhy Ave Des Plaines IL
Book a stay at this business-friendly hotel in Des Plaines. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff ...
8.2/10 Very Good! (291 reviews)
"Not very updated."

Reviewed on Sep 28, 2026

Get rates
Spark by Hilton Des Plaines Chicago O'Hare
Best Western Des Plaines/O’Hare

Best Western Des Plaines/O’Hare

2.5 out of 5
1231 Lee St Des Plaines IL
Stay at this hotel in Des Plaines. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Get rates
Best Western Des Plaines/O’Hare
Courtyard by Marriott Chicago O'Hare

Courtyard by Marriott Chicago O'Hare

3 out of 5
2950 S River Rd Des Plaines IL
Book a stay at this business-friendly hotel in Des Plaines. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.6/10 Excellent! (1,005 reviews)
"Everything was good. I couldn't get a receipt because the room was booked through Expedia."

Reviewed on Sep 28, 2026

Get rates
Courtyard by Marriott Chicago O'Hare
Extended Stay America Select Suites Chicago O'Hare

Extended Stay America Select Suites Chicago O'Hare

2.5 out of 5
1201 E Touhy Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Allstate Arena and Lake Park ...
6.8/10 (1,002 reviews)
"1 overnight here served the purpose. Dunno if I’d stay again but it wasn’t awful, just ok. Nice front desk staff but property desperately needs repairs a facelift especially the dank, dark ugly brown carpet. Lighting is from the Bates Motel. There is no shuttle from Ohare either."

Reviewed on Sep 27, 2026

Get rates
Extended Stay America Select Suites Chicago O'Hare
Extended Stay America Suites Chicago O'Hare Allstate Arena

Extended Stay America Suites Chicago O'Hare Allstate Arena

2.5 out of 5
1207 E Touhy Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. ...
7.6/10 Good! (1,003 reviews)
"The event we went to was next to it so we booked it asap. But the staff 1000/10! Erica was the kindest ! She helped us figure out the L. Helped us out with recommendations! Everyone was so kind!"

Reviewed on Sep 27, 2026

Get rates
Extended Stay America Suites Chicago O'Hare Allstate Arena
See all 4,892 properties in Des Plaines
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.