Gold Coast Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Gold Coast
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,501, price is now CA $988 per person
CA $988
per person
Jul 9 - Jul 13
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $1,564, price is now CA $1,004 per person
CA $1,004
per person
Jul 9 - Jul 13
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
Picked the hotel because it was supposed to be near Riviera theater. It really wasn't. Otherwise, it's a beautiful property. Staff are friendly and helpful. There's casual and fine dining at the location. Easy to get a cab if you don't have an app. Across from riverfront.
Reviewed on May 9, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,903, price is now CA $1,298 per person
CA $1,298
per person
Jul 23 - Jul 27
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026
Where to stay in Gold Coast
Find the best Gold Coast areas and neighborhoods for the activities you enjoy most. Learn more about Gold Coast
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Gold Coast Hotel Deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from May 21 to May 22
CA $210
CA $250 total
May 21 - May 22
includes taxes & fees
8.2/10 Very Good! (1,425 reviews)
A short walk to Lake Michigan, Magnificant Mile in a peaceful neighbourhood. The gallery in the basement is also worth checking out with rich cultural history. Architecture is great too！
Reviewed on May 8, 2026
Thompson Chicago, by Hyatt
21 East Bellevue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $243 per night from May 25 to May 26
CA $243
CA $330 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (1,364 reviews)
Clean and beautiful room. Friendly staff and close to many shops and sites.
Reviewed on May 8, 2026
Claridge House Chicago, Tapestry Collection by Hilton
1244 N Dearborn Parkway Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from May 10 to May 11
CA $149
CA $217 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (1,517 reviews)
Have stayed here often when it was Indigo. It was colorful and alive and the decor was welcoming. Also it had a valet service with garage next door. The staff of the claridge is excellent! The parking was next door, but no valet service with the hotel and no price reduction with the hotel. Parking ...
Reviewed on Apr 30, 2026
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.
Frequently asked questions
Discover the most popular places to visit in Gold Coast
International Museum of Surgical Science
You can spend time exploring the galleries in International Museum of Surgical Science during your trip to Chicago. Experience the acclaimed theater scene and entertainment choices in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
CA $61
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.