
Gilberts Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Gilberts Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

The Whitehall Hotel, BW Premier Collection
Downtown Chicago
$775
per person
Oct 1 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Clean property and friendly staff.
Reviewed on Aug 28, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
$1,165
per person
Oct 1 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 rooms, kind staff
Reviewed on Aug 28, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$1,244
per person
Oct 1 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Absolutely, better than amazing view of the Chicago view and lake. Rented the room for a special occasion that worked out great. After searching for other hotels in the area with a great view, this choice was the best choice I could have made. Since Navy Pier is one of Chicago biggest tourist attractions, I highly recommend a comfortable pair of walking shoes. I do think some of the furniture pieces should be updated to something more modern or stylish for the price of the room. It will make the vibe much better. That's my personal opinion. Service was amazing and staff was friendly and very helpful. Parking was very reasonable.
Reviewed on Aug 28, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
$1,055
per person
Oct 1 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
This hotel truly exceeded my expectations and checked every box. From the moment we arrived, the property felt luxurious, stylish, and beautifully maintained. The accommodations were wonderful, and the attention to detail throughout the hotel really made the stay feel special.
The location was also excellent and made it convenient to enjoy everything the area had to offer. The rooftop was absolutely magnificent, the bar had a great atmosphere, and our room was spotless and refreshed every day.
What stood out most was the way the staff cared for their guests. Everyone was friendly, attentive, welcoming, and always willing to help. I did experience one minor issue during my stay, but it was handled quickly and professionally, which I truly appreciated.
Everything seemed to run like a well-oiled machine. Between the luxurious atmosphere, great location, beautiful rooftop, cleanliness, and outstanding service, this was an exceptional stay. I will definitely be returning!
Reviewed on Aug 28, 2026

Eurostars Magnificent Mile
Downtown Chicago
$898
per person
Oct 1 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Clean room, property was in excellent location. Walkable to everything
Reviewed on Aug 28, 2026

Swissotel - Chicago
Downtown Chicago
$1,065
per person
Oct 1 - Oct 5
found 6 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 was awesome and will stay there again
Reviewed on Aug 28, 2026
Top Hotel Deals

Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Book a stay at this spa resort in Itasca. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...

The Westin Chicago Northwest
400 Park Blvd Itasca IL
Book a stay at this business-friendly hotel in Itasca. Enjoy breakfast (surcharge), a free area shuttle, and a 24-hour fitness center. Our guests praise the ...

Comfort Inn Chicago Schaumburg - O'Hare Airport
1300 E Higgins Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...

Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir Rolling Meadows IL
Stay at this motel in Rolling Meadows. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...

Hyatt Regency Schaumburg Chicago
1800 East Golf Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...

Quality Inn Schaumburg - Chicago near the Mall
600 North Martingale Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Days Inn & Suites by Wyndham Arlington Heights
1415 W Dundee Rd Arlington Heights IL
Book a stay at this business-friendly hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...

Hyatt Place Chicago/ Schaumburg
1851 McConnor Parkway Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

Country Inn & Suites by Radisson, Elk Grove Village/Itasca
1160 W Devon Avenue Elk Grove Village IL
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...

Renaissance Schaumburg Convention Center Hotel
1551 Thoreau Dr N Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff ...

Hilton Garden Inn Hoffman Estates
2425 Barrington Road Hoffman Estates IL
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...

Marriott Chicago Schaumburg
50 N Martingale Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff ...

Best Western Plus Elgin - Chicago
2175 Marriott Dr West Dundee IL
Book a stay at this business-friendly hotel in West Dundee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Geneva Motel Inn
100 South Tyler Rd St. Charles IL
Book a stay at this business-friendly hotel in St. Charles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...

Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
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.

Tue, Oct 13 - Thu, Oct 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 16 hours ago

Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183
Roundtrip
found 16 hours ago

Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$193
Roundtrip
found 16 hours ago

Thu, Oct 1 - Sun, Oct 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 5 days ago

Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$377
Roundtrip
found 1 day ago
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