Cheap Vacations in DuPage County

Choose two or more items and save on your trip:

DuPage County vacations

Price found within the past 48 hours. Click for updated prices.
Furness Mansion

Furness Mansion

2 out of 5
Price was $438, price is now $311 per person
$311
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,395, price is now $1,597 per person
$1,597
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,837, price is now $1,300 per person
$1,300
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
Price was $447, price is now $324 per person
$324
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $928, price is now $674 per person
$674
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was $900, price is now $683 per person
$683
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Price was $897, price is now $683 per person
$683
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,866, price is now $1,450 per person
$1,450
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Glen Club

The Glen Club

4 out of 5
Price was $711, price is now $557 per person
$557
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG

3.5 out of 5
Price was $419, price is now $329 per person
$329
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

3-night DuPage County vacations

Price found within the past 48 hours. Click for updated prices.
Furness Mansion

Furness Mansion

2 out of 5
Price was $438, price is now $311 per person
$311
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $2,395, price is now $1,597 per person
$1,597
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,510, price is now $1,052 per person
$1,052
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,837, price is now $1,300 per person
$1,300
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $689, price is now $497 per person
$497
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
Price was $447, price is now $324 per person
$324
per person
Oct 23 - Oct 26
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $928, price is now $674 per person
$674
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Price was $900, price is now $683 per person
$683
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
Price was $1,424, price is now $1,082 per person
$1,082
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Price was $897, price is now $683 per person
$683
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,255, price is now $962 per person
$962
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Save 100% on your flight
Price was $1,866, price is now $1,450 per person
$1,450
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

4-night DuPage County vacations

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

4 out of 5
Price was $711, price is now $557 per person
$557
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $936, price is now $618 per person
$618
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $2,807, price is now $1,886 per person
$1,886
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,303, price is now $876 per person
$876
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $1,441, price is now $1,008 per person
$1,008
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,129, price is now $812 per person
$812
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Arista

Hotel Arista

4.5 out of 5
Price was $837, price is now $607 per person
$607
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
La Banque Hotel

La Banque Hotel

4 out of 5
Price was $879, price is now $650 per person
$650
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,196, price is now $896 per person
$896
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $1,162, price is now $880 per person
$880
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
Price was $1,173, price is now $911 per person
$911
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Chicago Marriott Southwest at Burr Ridge

Chicago Marriott Southwest at Burr Ridge

4 out of 5
Price was $748, price is now $588 per person
$588
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

5-night DuPage County vacations

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Chicago SW - Burr Ridge by IHG

Crowne Plaza Chicago SW - Burr Ridge by IHG

4 out of 5
Price was $549, price is now $434 per person
$434
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Save 100% on your flight
Price was $1,555, price is now $1,068 per person
$1,068
per person
Oct 22 - Oct 27
just found
Roundtrip flight included
Oklahoma City (OKC) to Chicago (ORD)
Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Save 100% on your flight
Price was $1,097, price is now $799 per person
$799
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,117, price is now $819 per person
$819
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,504, price is now $1,107 per person
$1,107
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Price was $1,394, price is now $1,037 per person
$1,037
per person
Oct 22 - Oct 27
just found
Roundtrip flight included
Oklahoma City (OKC) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,753, price is now $1,310 per person
$1,310
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Freehand Chicago

Freehand Chicago

4 out of 5
Save 100% on your flight
Price was $1,056, price is now $799 per person
$799
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,641, price is now $1,255 per person
$1,255
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $1,353, price is now $1,039 per person
$1,039
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
Price was $1,720, price is now $1,354 per person
$1,354
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Save 100% on your flight
Price was $1,745, price is now $1,385 per person
$1,385
per person
Oct 15 - Oct 20
found 8 hours ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)

6-7 night DuPage County vacations

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
Price was $966, price is now $697 per person
$697
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Price was $2,520, price is now $1,387 per person
$1,387
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $1,861, price is now $1,045 per person
$1,045
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $2,872, price is now $1,826 per person
$1,826
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $2,244, price is now $1,472 per person
$1,472
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Price was $2,251, price is now $1,491 per person
$1,491
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Ohio House Motel

Ohio House Motel

3 out of 5
Price was $1,382, price is now $948 per person
$948
per person
Oct 2 - Oct 8
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $2,246, price is now $1,540 per person
$1,540
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $2,309, price is now $1,615 per person
$1,615
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $2,530, price is now $1,824 per person
$1,824
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,179, price is now $1,596 per person
$1,596
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
Save 100% on your flight
Price was $2,157, price is now $1,587 per person
$1,587
per person
Oct 11 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Flight deals to DuPage County

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

Wed, Oct 21 - Sat, Oct 24
LAX
Los Angeles
ORD
Chicago
$128 Roundtrip, found 22 hours ago
$128
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Los Angeles to Chicago, returning Sat, Oct 24, priced at $128 found 22 hours ago
Thu, Nov 12 - Sun, Nov 15
LAX
Los Angeles
ORD
Chicago
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select United flight, departing Thu, Nov 12 from Los Angeles to Chicago, returning Sun, Nov 15, priced at $197 found 5 days ago
Wed, Sep 30 - Sun, Oct 4
LAX
Los Angeles
MDW
Chicago
$207 Roundtrip, found 5 days ago
$207
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Sep 30 from Los Angeles to Chicago, returning Sun, Oct 4, priced at $207 found 5 days ago

Top rated hotels for your DuPage County vacation

Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Free Cancellation
Reserve now, pay when you stay
8.94 mi from city center
$64 nightly
The price is $71 total per night
$71 total
Sep 27 - Sep 28
Total with taxes and fees
Located in Westmont, Chicago Club Inn & Suites is in the suburbs, a 5-minute drive from Oakbrook Center Mall and 8 minutes from Yorktown Shopping Center.
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Free Cancellation
Reserve now, pay when you stay
11.6 mi from city center
$63 nightly
The price is $70 total per night
$70 total
Sep 6 - Sep 7
Total with taxes and fees
With a stay at Red Roof Inn PLUS+ Chicago - Willowbrook in Willowbrook, you'll be in the suburbs, within a 10-minute drive of Oakbrook Center Mall and Willowbrook Community Park.
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
1401 Nordic Rd Itasca IL
Free Cancellation
Reserve now, pay when you stay
7.4 mi from city center
$135 nightly
The price is $150 total per night
$150 total
Aug 30 - Aug 31
Total with taxes and fees
Located in Itasca, Eaglewood Resort and Spa is in the suburbs, within a 10-minute drive of Bloomingdale Park District Museum and The Oasis Water Park.
Don't see what you're looking for?
See all available properties in DuPage County
View all properties
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.