Old Town Chicago Vacations from $527
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Your Old Town Chicago Vacation
Experience the best that Old Town Chicago has to offer with a tailor-made Old Town Chicago vacation package. From its cafes and bars and pubs to its history, you'll quickly fall for the charms of this commercial neighborhood. When it's time to see the sights, you'll find lots of big-name attractions nearby including Wrigley Field, Millennium Park and Willis Tower. Tick off one, two or all during your trip to Old Town Chicago. Expedia will help turn your ideal Old Town Chicago vacation into reality, no matter your travel plans or budget.
The Latest Old Town Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $790, price is now $527 per person
$527
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
Staff are friendly. Facility is not as clean. Elevator does not look like being cleaned often. My room is so oddly set up. The refrigerator and microwave is blocking the small closet which has the cloth steamer set up five feet up. The microwave cable is actually blocking the closet. No coffee maker. No cups. Charge $5 each luggage to keep temporarily after check out.
Reviewed on Jul 6, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,180, price is now $724 per person
$724
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
The property was amazing including the buffet breakfast.
Reviewed on Jul 6, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,342, price is now $885 per person
$885
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,315, price is now $880 per person
$880
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Amazing hotel and you can't beat the Navy Pier location.
Reviewed on Jul 5, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,162, price is now $777 per person
$777
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
This was a very clean and nice hotel. I enjoyed the room.
Reviewed on Jul 6, 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
$144 nightly
The price is $171 total per night from Jul 7 to Jul 8
$171 total
Jul 7 - Jul 8
Total with taxes and fees
8.2/10 Very Good! (1,695 reviews)
"Tried to use the very small hair dryer only to find out it quite in a puff of black smoke and smelled up the whole room."
Reviewed on Jul 5, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $229 total per night from Jul 8 to Jul 9
$229 total
Jul 8 - Jul 9
Total with taxes and fees
8/10 Very Good! (10,178 reviews)
"This will always be my go to place to stay in downtown Chicago. Fantastic location, clean and great staff."
Reviewed on Jul 6, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$242 nightly
The price is $284 total per night from Jul 11 to Jul 12
$284 total
Jul 11 - Jul 12
Total with taxes and fees
8.4/10 Very Good! (2,322 reviews)
"Location- staff- restaurant- excellent customer service."
Reviewed on Jul 5, 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.
Stay near popular Old Town Chicago attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.