Chicago Adventure Vacation Packages
Best Chicago Adventure packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Sep 3 - Sep 6
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, 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.
Great place will stay again
Reviewed on Jul 27, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 3 - Sep 6
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry was historic and great
Reviewed on Jul 5, 2024
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Sep 3 - Sep 6
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Family friendly, Close proximity to land marks , dining, entertainment
Reviewed on Jul 30, 2025
3 night Chicago Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Oct 4 - Oct 7
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Family friendly, Close proximity to land marks , dining, entertainment
Reviewed on Jul 30, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 3 - Sep 6
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry was historic and great
Reviewed on Jul 5, 2024
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 4 - Oct 7
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
We came to town for a wedding and loved the location of the Palmer House. We spent much of the day before the event walking the city and sightseeing. It is a beautiful hotel.
Reviewed on Jul 28, 2025
4 night Chicago Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Oct 4 - Oct 8
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Family friendly, Close proximity to land marks , dining, entertainment
Reviewed on Jul 30, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Oct 4 - Oct 8
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!
Reviewed on Jun 15, 2025
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 4 - Oct 8
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
We came to town for a wedding and loved the location of the Palmer House. We spent much of the day before the event walking the city and sightseeing. It is a beautiful hotel.
Reviewed on Jul 28, 2025
5 night Chicago Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Oct 4 - Oct 9
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!
Reviewed on Jun 15, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Oct 4 - Oct 9
found 16 hours ago
Roundtrip flight included
Phoenix (PHX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry was historic and great
Reviewed on Jul 5, 2024
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 5 - Oct 10
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The best hotel in Chicago!
Reviewed on Jul 4, 2025
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Downtown Chicago
Save 100% on your flight
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Liked everything about this hotel and have stayed here a few times. Wish the gym was a little more up to date.
Reviewed on May 27, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The best hotel in Chicago!
Reviewed on Jul 4, 2025
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Save 100% on your flight
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The location of the Intercontinental Magnificent Mile, Chicago cannot be better. It’s literally right smack dab in the middle of everything. We had an amazing weekend there. The room was comfortable and clean. The staff was friendly and we didn’t wait for anything we needed. Highly recommend, 10/10. Oh the pool is worth just asking a walk through. Super cool.
Reviewed on Jul 21, 2025
Adventure hotels in Chicago
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$198 nightly
The price is $229 total per night
$229 total
Aug 21 - Aug 22
Total includes taxes and fees
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with access to locker space, concierge services, and dry cleaning/laundry. Other amenities at this spa hotel include a conference center, a business center, and express check-in.
Pool
Spa
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$209 nightly
The price is $245 total per night
$245 total
Aug 20 - Aug 21
Total includes taxes and fees
Guests of Hyatt Regency McCormick Place Chicago have access to an indoor pool, a gym, and a sauna. Parking is available for USD 40 per night (USD 60 per day for valet parking), and there's also a free casino shuttle. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, concierge services, and securing valuables. Additional amenities include free WiFi in public areas, meeting rooms, and a conference center.
Pool
Free WiFi
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$279 nightly
The price is $328 total per night
$328 total
Aug 21 - Aug 22
Total includes taxes and fees
Guests of Hyatt Regency Chicago enjoy a gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 87 per night. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, securing valuables, and tours or tickets. Additional amenities include conference space, a business center, and express check-in.
Free WiFi
Restaurant
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.
How much does it cost to fly to Chicago?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$60 Roundtrip, found 3 days ago
$60
Roundtrip
found 3 days ago
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
LGA
LaGuardia
ORD
O'Hare Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$70 Roundtrip, found 4 days ago
$70
Roundtrip
found 4 days ago
SAN
San Diego Intl.
ORD
O'Hare Intl.
$86 Roundtrip, just found
$86
Roundtrip
just found
IAH
George Bush Intercontinental
MDW
Midway Intl.
$95 Roundtrip, found 5 days ago
$95
Roundtrip
found 5 days ago
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$96 Roundtrip, just found
$96
Roundtrip
just found
LGA
LaGuardia
MDW
Midway Intl.
$119 Roundtrip, found 6 days ago
$119
Roundtrip
found 6 days ago
SAN
San Diego Intl.
MDW
Midway Intl.
$139 Roundtrip, found 10 hours ago
$139
Roundtrip
found 10 hours ago
CLD
McClellan-Palomar
ORD
O'Hare Intl.
$161 Roundtrip, found 6 hours ago
$161
Roundtrip
found 6 hours ago
OMA
Eppley Field
ORD
O'Hare Intl.
$180 Roundtrip, found 20 hours ago
$180
Roundtrip
found 20 hours ago
OMA
Eppley Field
MDW
Midway Intl.
$180 Roundtrip, found 5 days ago
$180
Roundtrip
found 5 days ago
LGA
LaGuardia
RFD
Greater Rockford
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Hotel themes
- Hotels with WiFi in Chicago
- Kid Friendly Hotels in Chicago
- Hotels with Restaurants in Chicago
- Business Hotels in Chicago
- Hotels with a Gym in Chicago
- Hotels with Free Parking in Chicago
- Hotels with Bar in Chicago
- Hotels with Free Breakfast in Chicago
- Hotels with Pool in Chicago
- Cheap Hotels in Chicago