Dolton Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Dolton Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Blackstone, Autograph Collection
Downtown Chicago
Price was $968, price is now $765 per person
$765
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,375, price is now $939 per person
$939
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Clean room, excellent location and free breakfast! Most tourist areas are under a 20 minute walk
Reviewed on Nov 10, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,222, price is now $893 per person
$893
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,942, price is now $1,430 per person
$1,430
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
i love it
Reviewed on Nov 10, 2026
Swissotel - Chicago
Downtown Chicago
Price was $1,165, price is now $882 per person
$882
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury 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.
Everything very nice it is centered where u can go to a lot of attractions
Reviewed on Nov 10, 2026
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,972, price is now $1,547 per person
$1,547
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip flight included
Washington (WAS) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
This place was amazing and the hotel staff was extremely helpful
Reviewed on Nov 10, 2026
Top Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
27.43 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
30.86 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
River Hotel
75 East Wacker Drive Chicago IL
28.84 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Wade
644 N Lake Shore Dr Chicago IL
29.47 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
29.71 km from city center
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Hilton Chicago
720 S Michigan Ave Chicago IL
27.13 km from city center
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
27.99 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the ...
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
28.81 km from city center
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
28.63 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Eurostars Magnificent Mile
660 North State Street Chicago IL
29.57 km from city center
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
The Godfrey Hotel Chicago
127 West Huron, at LaSalle Chicago IL
29.66 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
28.71 km from city center
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
Freehand Chicago
19 East Ohio Street Chicago IL
29.34 km from city center
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Jan 29 - Wed, Feb 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$294 Roundtrip, just found
$294
Roundtrip
just found
Fri, Jan 29 - Wed, Feb 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$297 Roundtrip, just found
$297
Roundtrip
just found
Fri, Jan 29 - Wed, Feb 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$302 Roundtrip, just found
$302
Roundtrip
just found
Fri, Jan 29 - Wed, Feb 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$302 Roundtrip, just found
$302
Roundtrip
just found
Fri, Jan 29 - Wed, Feb 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$329 Roundtrip, just found
$329
Roundtrip
just found