Old Town Chicago Vacation Packages
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Top Holiday Package Deals in Old Town Chicago
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,372, price is now CA $969 per person
CA $969
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
The rooms were spotless and very well tended to. My wife and I really enjoyed how central it was to many stores, restaurants, and places of interest. We also enjoyed the bar, with its selection of great drinks; it was a great way to relax after walking around Chicago all day!
Reviewed on Jul 4, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,606, price is now CA $1,064 per person
CA $1,064
per person
Sep 4 - Sep 7
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.
Reviewed on Jul 2, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,895, price is now CA $1,263 per person
CA $1,263
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,573, price is now CA $1,809 per person
CA $1,809
per person
Aug 7 - Aug 11
found 20 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,734, price is now CA $1,987 per person
CA $1,987
per person
Sep 4 - Sep 7
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026
Where to stay in Old Town Chicago
Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Chicago
Downtown Chicago
5 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.
Old Town Chicago 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 $204 per night from Jul 6 to Jul 7
CA $204
CA $243 total
Jul 6 - Jul 7
includes taxes & fees
8.2/10 Very good! (1,684 reviews)
"Absolutely wonderful experience staying here beautiful view of the city. Complimentary breakfast was wonderful and extremely friendly and helpful staff. Highly recommend staying here"
Reviewed on Jul 3, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Jul 6 to Jul 7
CA $172
CA $205 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very good! (10,146 reviews)
"We got in pretty late. The front desk staff that assisted us barely put more than 5 words together. He didn’t give any information..most of all the things that didn’t work/broken. The room was extremely small, the bathroom so tight if you closed the door while on the toilet your knees would be jammed ..."
Reviewed on Jul 3, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $368 per night from Jul 5 to Jul 6
CA $368
CA $432 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very good! (2,319 reviews)
"Very convenient location for a short stay"
Reviewed on Jul 4, 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
Stay near popular Old Town Chicago attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.