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The 606 Vacation Packages

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The 606 Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Chicago O'Hare Airport

Four Points by Sheraton Chicago O'Hare Airport

3 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 18
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Allstate Arena and Fashion Outlets of Chicago are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms 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
per person
Jul 23 - Jul 27
found 6 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3-star hotel in Lake Geneva. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Geneva Lake and Lake Geneva Cruise Line are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
per person
Jul 11 - Jul 18
found 20 hours ago
Roundtrip flight included
Boston (BOS) 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago/Midway Airport

Hilton Garden Inn Chicago/Midway Airport

3 out of 5
Save 100% on your flight
per person
Jul 4 - Jul 9
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Save 100% on your flight
per person
Jul 15 - Jul 20
found 24 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Chicago Riverwalk and United Center are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
Jul 17 - Jul 21
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
Save 100% on your flight
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

3-4 Night Vacations in The 606

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
per person
Jul 23 - Jul 27
found 6 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 24 - Jul 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

5-7 Night Vacations in The 606

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
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 27
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
Downtown Chicago
Save 100% on your flight
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)

The 606 Last Minute Hotel Deals

The Robey, Chicago, a Member of Design Hotels
The Robey, Chicago, a Member of Design Hotels
3.5 out of 5
2018 W. North Ave., Chicago, IL
Stay at this 3.5-star hotel in Chicago. Enjoy an outdoor pool, 3 bars/lounges, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular ...
The Robey, Chicago, a Member of Design Hotels
Ray's Bucktown B&B
Ray's Bucktown B&B
3.5 out of 5
2144 N. Leavitt St, Chicago, IL
Stay at this 3.5-star business-friendly B&B in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Ray's Bucktown B&B
The Hotel at Midtown
The Hotel at Midtown
4 out of 5
2444 N. Elston Ave, Chicago, IL
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
The Hotel at Midtown
Stay 424 Hostel
Stay 424 Hostel
2 out of 5
1415 Ashland Ave, Chicago, IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour business center, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular ...
Stay 424 Hostel
Hyatt Place Chicago/Wicker Park
Hyatt Place Chicago/Wicker Park
3 out of 5
1551 West North Ave, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Our guests praise the breakfast and the bar in our ...
Hyatt Place Chicago/Wicker Park
Wicker Park Inn
Wicker Park Inn
3.5 out of 5
1331 N Wicker Park Ave, Chicago, IL
Stay at this 3.5-star business-friendly B&B in Chicago. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the helpful staff in our ...
Wicker Park Inn
Chicago Avenue Inn
Chicago Avenue Inn
2 out of 5
3305 W Chicago Ave, Chicago, IL
Stay at this guesthouse in Chicago. Enjoy free WiFi, housekeeping, and air conditioning. Popular attractions United Center and Chicago Riverwalk are located ...
Chicago Avenue Inn
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
citizenM Chicago Downtown
See all 4,180 properties in The 606
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.