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Sycamore Vacation Packages

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Sycamore Flight + Hotel Packages

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
Save 100% on your flight
Price was $274, price is now $147 per person
$147
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Price was $1,440, price is now $520 per person
$520
per person
Dec 23 - Dec 28
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Price was $392, price is now $172 per person
$172
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Price was $421, price is now $188 per person
$188
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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
Price was $408, price is now $205 per person
$205
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Price was $729, price is now $374 per person
$374
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $531, price is now $280 per person
$280
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
Price was $552, price is now $302 per person
$302
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this hotel in Lake Geneva. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff in our reviews. Popular attractions Geneva National Golf Club and Lake Como are located nearby.

Sycamore Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was $392, price is now $172 per person
$172
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $421, price is now $188 per person
$188
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,249, price is now $597 per person
$597
per person
Dec 23 - Dec 27
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $408, price is now $205 per person
$205
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Sycamore Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
Downtown Chicago
Price was $704, price is now $358 per person
$358
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,440, price is now $520 per person
$520
per person
Dec 23 - Dec 28
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $946, price is now $424 per person
$424
per person
Feb 12 - Feb 17
found 18 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,300, price is now $682 per person
$682
per person
Feb 12 - Feb 17
found 18 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Chicago (ORD)

Top Flight Deals

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

American Airlines
Sat, Feb 14 - Tue, Feb 17
MCO
Orlando Intl.
RFD
Greater Rockford
$139 Roundtrip, found 7 hours ago
$139
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Feb 14 from Orlando Intl. to Greater Rockford, returning Tue, Feb 17, priced at $139 found 7 hours ago
American Airlines
Tue, Feb 17 - Thu, Feb 19
LAS
Harry Reid Intl.
RFD
Greater Rockford
$159 Roundtrip, found 4 days ago
$159
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Feb 17 from Harry Reid Intl. to Greater Rockford, returning Thu, Feb 19, priced at $159 found 4 days ago
American Airlines
Thu, Dec 11 - Mon, Dec 15
TPA
Tampa Intl.
RFD
Greater Rockford
$171 Roundtrip, found 4 days ago
$171
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Dec 11 from Tampa Intl. to Greater Rockford, returning Mon, Dec 15, priced at $171 found 4 days ago
American Airlines
Wed, Nov 26 - Sun, Nov 30
MSP
Minneapolis - St. Paul Intl.
RFD
Greater Rockford
$410 Roundtrip, found 5 days ago
$410
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Nov 26 from Minneapolis - St. Paul Intl. to Greater Rockford, returning Sun, Nov 30, priced at $410 found 5 days ago