Cheap Vacations in DuPage County

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DuPage County vacations

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Glenview

Baymont by Wyndham Glenview

3 out of 5
Price was $498, price is now $368 per person
$368
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,410, price is now $891 per person
$891
per person
Jul 22 - Jul 26
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 $1,585, price is now $1,066 per person
$1,066
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $861, price is now $600 per person
$600
per person
Jul 29 - Jul 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,008, price is now $707 per person
$707
per person
Jul 21 - Jul 24
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $947, price is now $691 per person
$691
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,559, price is now $1,141 per person
$1,141
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,765, price is now $1,296 per person
$1,296
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,047, price is now $770 per person
$770
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
Price was $710, price is now $534 per person
$534
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

3-night DuPage County vacations

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Glenview

Baymont by Wyndham Glenview

3 out of 5
Price was $498, price is now $368 per person
$368
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $975, price is now $631 per person
$631
per person
Aug 5 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $638, price is now $416 per person
$416
per person
Aug 5 - Aug 8
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 $1,578, price is now $1,036 per person
$1,036
per person
Jul 30 - Aug 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,055, price is now $721 per person
$721
per person
Aug 6 - Aug 9
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 $1,008, price is now $707 per person
$707
per person
Jul 21 - Jul 24
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,281, price is now $899 per person
$899
per person
Jul 30 - Aug 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,284, price is now $902 per person
$902
per person
Jul 30 - Aug 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,479, price is now $1,048 per person
$1,048
per person
Jul 30 - Aug 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,437, price is now $1,019 per person
$1,019
per person
Jul 30 - Aug 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,749, price is now $1,267 per person
$1,267
per person
Jul 30 - Aug 2
found 2 days 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 $1,450, price is now $1,051 per person
$1,051
per person
Jul 30 - Aug 2
found 2 days 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $706, price is now $459 per person
$459
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $940, price is now $576 per person
$576
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,410, price is now $891 per person
$891
per person
Jul 22 - Jul 26
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 $1,585, price is now $1,066 per person
$1,066
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Save 100% on your flight
Price was $962, price is now $683 per person
$683
per person
Aug 10 - Aug 14
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 $947, price is now $691 per person
$691
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,559, price is now $1,141 per person
$1,141
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,765, price is now $1,296 per person
$1,296
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $1,047, price is now $770 per person
$770
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
Save 100% on your flight
Price was $680, price is now $501 per person
$501
per person
Aug 5 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
Save 100% on your flight
Price was $643, price is now $476 per person
$476
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Save 100% on your flight
Price was $1,276, price is now $975 per person
$975
per person
Jul 23 - Jul 27
found 10 hours 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.
The Westin Chicago Lombard

The Westin Chicago Lombard

4 out of 5
Save 100% on your flight
Price was $843, price is now $614 per person
$614
per person
Jul 29 - Aug 3
found 16 hours 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 $2,173, price is now $1,335 per person
$1,335
per person
Jul 29 - Aug 3
found 16 hours 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 $2,532, price is now $1,565 per person
$1,565
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,933, price is now $1,215 per person
$1,215
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,043, price is now $1,360 per person
$1,360
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Save 100% on your flight
Price was $1,529, price is now $1,026 per person
$1,026
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,665, price is now $1,123 per person
$1,123
per person
Jul 29 - Aug 3
found 16 hours 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 $1,553, price is now $1,100 per person
$1,100
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $2,879, price is now $2,050 per person
$2,050
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,980, price is now $1,463 per person
$1,463
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) 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 $1,978, price is now $1,468 per person
$1,468
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Save 100% on your flight
Price was $1,642, price is now $1,220 per person
$1,220
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

6-7 night DuPage County vacations

Price found within the past 48 hours. Click for updated prices.
River Hotel

River Hotel

4 out of 5
Save 100% on your flight
Price was $1,002, price is now $686 per person
$686
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,560, price is now $995 per person
$995
per person
Jul 23 - Jul 29
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $1,660, price is now $1,200 per person
$1,200
per person
Jul 23 - Jul 29
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Save 100% on your flight
Price was $1,785, price is now $1,307 per person
$1,307
per person
Jul 23 - Jul 29
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Ohio House Motel

Ohio House Motel

3 out of 5
Save 100% on your flight
Price was $1,447, price is now $1,074 per person
$1,074
per person
Jul 23 - Jul 29
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,489, price is now $876 per person
$876
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,642, price is now $1,007 per person
$1,007
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,419, price is now $906 per person
$906
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,366, price is now $893 per person
$893
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Save 100% on your flight
Price was $1,098, price is now $723 per person
$723
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 $1,230, price is now $842 per person
$842
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $2,038, price is now $1,420 per person
$1,420
per person
Jul 30 - Aug 4
found 7 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Flight deals to DuPage County

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

Sat, Aug 1 - Wed, Aug 5
LAX
Los Angeles
ORD
Chicago
$211 Roundtrip, found 15 hours ago
$211
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Aug 1 from Los Angeles to Chicago, returning Wed, Aug 5, priced at $211 found 15 hours ago
Tue, Aug 4 - Sat, Aug 8
LAX
Los Angeles
MDW
Chicago
$240 Roundtrip, found 12 hours ago
$240
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Los Angeles to Chicago, returning Sat, Aug 8, priced at $240 found 12 hours ago
Thu, Aug 27 - Wed, Sep 2
LAX
Los Angeles
ORD
Chicago
$243 Roundtrip, found 2 days ago
$243
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Thu, Aug 27 from Los Angeles to Chicago, returning Wed, Sep 2, priced at $243 found 2 days ago

Top rated hotels for your DuPage County vacation

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
24.99 mi from city center
$136 nightly
The price is $162 total per night
$162 total
Jun 29 - Jun 30
Total with taxes and fees
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
15.18 mi from city center
$135 nightly
The price is $154 total per night
$154 total
Jun 28 - Jun 29
Total with taxes and fees
With a stay at Hyatt Regency O'Hare Chicago in Rosemont, you'll be connected to the convention center, a 5-minute walk from Donald E. Stephens Convention Center and a 5-minute drive from Allstate Arena.
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free Cancellation
25.15 mi from city center
$131 nightly
The price is $155 total per night
$155 total
Jun 29 - Jun 30
Total with taxes and fees
With a stay at The Chicago Hotel Collection - Magnificent Mile in Chicago (Downtown Chicago), you'll be steps from Ann and Robert H. Lurie Children's Hospital and 5 minutes by foot from Museum of Contemporary Art Chicago.
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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.