Cheap Vacations in DuPage County

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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
Downtown Chicago
Save 100% on your flight
Price was $689, price is now $462 per person
$462
per person
Aug 6 - Aug 9
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 $1,075, price is now $682 per person
$682
per person
Aug 6 - Aug 9
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 $1,032, price is now $701 per person
$701
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
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)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $800, price is now $557 per person
$557
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
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 17 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,431, price is now $1,039 per person
$1,039
per person
Aug 6 - Aug 9
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
Downtown Chicago
Save 100% on your flight
Price was $1,071, price is now $785 per person
$785
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $786, price is now $581 per person
$581
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $965, price is now $719 per person
$719
per person
Aug 6 - Aug 9
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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $689, price is now $462 per person
$462
per person
Aug 6 - Aug 9
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 $1,075, price is now $682 per person
$682
per person
Aug 6 - Aug 9
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 $1,032, price is now $701 per person
$701
per person
Aug 6 - Aug 9
found 1 day 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)
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Save 100% on your flight
Price was $800, price is now $557 per person
$557
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 17 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 $798, price is now $579 per person
$579
per person
Aug 6 - Aug 9
found 1 day 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 $1,431, price is now $1,039 per person
$1,039
per person
Aug 6 - Aug 9
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 $1,071, price is now $785 per person
$785
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $786, price is now $581 per person
$581
per person
Aug 6 - Aug 9
found 1 day 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 $965, price is now $719 per person
$719
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Price was $657, price is now $490 per person
$490
per person
Aug 6 - Aug 9
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.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $1,081, price is now $805 per person
$805
per person
Jul 21 - Jul 25
found 19 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,369, price is now $922 per person
$922
per person
Jul 23 - Jul 27
found 20 hours 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 $1,756, price is now $1,286 per person
$1,286
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,888, price is now $1,394 per person
$1,394
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $1,439, price is now $1,073 per person
$1,073
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $1,605, price is now $1,199 per person
$1,199
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 $1,113, price is now $834 per person
$834
per person
Jul 23 - Jul 27
found 20 hours 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 $2,213, price is now $1,667 per person
$1,667
per person
Jul 23 - Jul 27
found 20 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 $1,276, price is now $975 per person
$975
per person
Jul 23 - Jul 27
found 20 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 $1,788, price is now $1,393 per person
$1,393
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Save 100% on your flight
Price was $1,749, price is now $1,379 per person
$1,379
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,143, price is now $914 per person
$914
per person
Jul 23 - Jul 27
found 20 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 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 $2,173, price is now $1,335 per person
$1,335
per person
Jul 29 - Aug 3
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 $2,532, price is now $1,565 per person
$1,565
per person
Jul 29 - Aug 3
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 $1,933, price is now $1,215 per person
$1,215
per person
Jul 29 - Aug 3
found 1 day 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 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 $1,529, price is now $1,026 per person
$1,026
per person
Jul 29 - Aug 3
found 1 day 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 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 $1,553, price is now $1,100 per person
$1,100
per person
Jul 29 - Aug 3
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 $2,879, price is now $2,050 per person
$2,050
per person
Jul 29 - Aug 3
found 1 day 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 1 day 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 1 day 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 1 day 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.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $1,359, price is now $984 per person
$984
per person
Jul 23 - Jul 29
found 18 hours 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 18 hours 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 $2,167, price is now $1,433 per person
$1,433
per person
Jul 23 - Jul 29
found 18 hours 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 $2,132, price is now $1,418 per person
$1,418
per person
Jul 23 - Jul 29
found 18 hours 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 $1,923, price is now $1,292 per person
$1,292
per person
Jul 23 - Jul 29
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $1,577, price is now $1,134 per person
$1,134
per person
Jul 23 - Jul 29
found 18 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 18 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 18 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 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Arlo Chicago

Arlo Chicago

4 out of 5
Save 100% on your flight
Price was $1,670, price is now $1,251 per person
$1,251
per person
Jul 23 - Jul 29
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
River Hotel

River Hotel

4 out of 5
Save 100% on your flight
Price was $1,611, price is now $1,210 per person
$1,210
per person
Jul 23 - Jul 29
found 18 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Save 100% on your flight
Price was $1,552, price is now $1,172 per person
$1,172
per person
Jul 23 - Jul 29
found 18 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.

Tue, Jul 21 - Wed, Jul 22
LAX
Los Angeles
ORD
Chicago
$211 Roundtrip, found 2 hours ago
$211
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Los Angeles to Chicago, returning Wed, Jul 22, priced at $211 found 2 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
Tue, Aug 4 - Sat, Aug 8
LAX
Los Angeles
MDW
Chicago
$256 Roundtrip, found 2 hours ago
$256
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Los Angeles to Chicago, returning Sat, Aug 8, priced at $256 found 2 hours 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.
Free WiFi
Restaurant
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.
Free airport shuttle
Pet friendly
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.