Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
La Banque Hotel
9.4/10 Exceptional! (520 reviews)
Sep 11 - Sep 14
3 night stay
Fort Lauderdale (FLL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $708, price is now $498 per person
$498
per person
found 22 hours ago
The hotel was closed due to no power. I was not able to check in as they were not open. Why did you take my reservation. I need my money back!!!
Reviewed on Jul 31, 2026
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (540 reviews)
Oct 22 - Oct 26
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,461, price is now $939 per person
$939
per person
found 1 day ago
Comes with all the comforts of
Home.
Reviewed on Jul 29, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,770 reviews)
Sep 15 - Sep 19
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • FirstClass
Save 100% on your flight
Price was $2,658, price is now $1,722 per person
$1,722
per person
found 1 day ago
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,858 reviews)
Oct 17 - Oct 19
2 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Frontier Airlines • Non-stop • Coach
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $729, price is now $511 per person
$511
per person
found 1 day ago
fabulous location and helpful staff.
Reviewed on Aug 1, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,606 reviews)
Sep 15 - Sep 19
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • FirstClass
Save 100% on your flight
Price was $2,301, price is now $1,616 per person
$1,616
per person
found 1 day ago
I didn't like the fact that the staff never explained the amenities in its entirety. Also, when I was using a rideshare I asked the front desk for directions and the lady pointed me in the wrong direction. I should have known better by how fast and confuse her face looked when she responded to my question. I just hate the fact that I trusted her response. Most importantly the $29 daily fee was never mentioned upon check-in; I later found out that it was on a card the size of a room key that was handed to me during check-in. I will say the location was extremely clean and offered awesome views. Ultimately, if I had to stay again knowing all I know now I would stay again.
Reviewed on Aug 1, 2026
Top rated hotels for your Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$145 nightly
The price is $172 total per night
$172 total
Aug 30 - Aug 31
Total with taxes and fees
Guests of Congress Plaza Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 62.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, concierge services, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.74 mi from city center
$152 nightly
The price is $181 total per night
$181 total
Aug 11 - Aug 12
Total with taxes and fees
Guests of The Chicago Hotel Collection Ambassador Gold Coast enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 75 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, express check-out, and a banquet hall.
Pet friendly
Free WiFi
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
13.75 mi from city center
$169 nightly
The price is $193 total per night
$193 total
Aug 30 - Aug 31
Total with taxes and fees
At Hyatt Regency O'Hare Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. If you drive, self parking is USD 45 per night, or you can take advantage of the free airport shuttle (available 24 hours). Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and a microwave in a common area.
Free airport shuttle
Pet friendly
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.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
$36
per child
88% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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