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Irwin Vacation Packages

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Irwin Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago North Shore/Evanston

Hilton Garden Inn Chicago North Shore/Evanston

3.5 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 9
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Aragon Ballroom and Riviera Theatre are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
per person
May 17 - May 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Save 100% on your flight
per person
May 17 - May 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
May 17 - May 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Save 100% on your flight
per person
May 17 - May 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Irwin Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Apr 18 - Apr 21
found 5 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 16 - May 19
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 22 - May 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)

Irwin Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
May 5 - May 11
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 17 - May 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 5 - May 11
found 9 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)

Top Flight Deals

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

Spirit Airlines
Wed, Apr 23 - Tue, Apr 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$126 Roundtrip, just found
$126
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Apr 23 from Los Angeles Intl. to O'Hare Intl., returning Tue, Apr 29, priced at $126 just found
Frontier Airlines
Tue, Apr 29 - Wed, May 7
LAX
Los Angeles Intl.
MDW
Midway Intl.
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Apr 29 from Los Angeles Intl. to Midway Intl., returning Wed, May 7, priced at $150 found 4 days ago
United
Wed, Apr 23 - Sat, Apr 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$181 Roundtrip, just found
$181
Roundtrip
just found
Select United flight, departing Wed, Apr 23 from Los Angeles Intl. to O'Hare Intl., returning Sat, Apr 26, priced at $181 just found
LOT-Polish Airlines
Thu, Mar 20 - Tue, Apr 1
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$754 Roundtrip, found 19 hours ago
$754
Roundtrip
found 19 hours ago
Select LOT-Polish Airlines flight, departing Thu, Mar 20 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Tue, Apr 1, priced at $754 found 19 hours ago