Illinois Adventure Vacation Packages
Best Illinois Adventure packages
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $903, price is now $631 per person
$631
per person
Jul 17 - Jul 20
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The excellent hotel launch our vacation in Chicago. The rooms were modern and comfortable. Did you help?
Reviewed on Jun 12, 2026
Kinzie Hotel
Downtown Chicago
Price was $854, price is now $684 per person
$684
per person
Jul 17 - Jul 20
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The room smelled and the awful noise from the bathroom exhaust fan was annoying.
Reviewed on Mar 2, 2026
Hotel 55 Chicago Downtown
Downtown Chicago
Price was $948, price is now $770 per person
$770
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour 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.
didnt have breakfast. convenient to my meetings
Reviewed on Nov 21, 2025
3 night Illinois Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was $735, price is now $550 per person
$550
per person
Aug 18 - Aug 21
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 4 restaurants, and a rooftop terrace. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
First time staying here in downtown Chicago. Loved the ambiance and vibe of this hotel! Not to mention, the close proximity to the downtown events we wanted to check out!!!
Reviewed on Apr 24, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $903, price is now $631 per person
$631
per person
Jul 17 - Jul 20
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The excellent hotel launch our vacation in Chicago. The rooms were modern and comfortable. Did you help?
Reviewed on Jun 12, 2026
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,783, price is now $1,368 per person
$1,368
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip flight included
Sacramento (SMF) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Everything was superb. The only “complaint “ I have, is that I paid for a city view room, but actually looked at the side of one building. Other than that, we lived the stay.
Reviewed on Oct 24, 2025
4 night Illinois Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $655, price is now $412 per person
$412
per person
Aug 17 - Aug 21
found 14 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The two main complaints that I have is that there wasn’t a full length mirror anywhere and no complementary bottles of water in the room. Other than that, the beds were fantastic. The sheets were great. The pillows were awesome and the staff was terrific.
Reviewed on Jun 9, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $719, price is now $470 per person
$470
per person
Aug 17 - Aug 21
found 14 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The excellent hotel launch our vacation in Chicago. The rooms were modern and comfortable. Did you help?
Reviewed on Jun 12, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $806, price is now $545 per person
$545
per person
Aug 17 - Aug 21
found 14 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The bell hoppers were all very pleasant each and every time we left and came back inside!
Reviewed on May 16, 2026
5 night Illinois Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $954, price is now $573 per person
$573
per person
Aug 17 - Aug 22
just found
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The two main complaints that I have is that there wasn’t a full length mirror anywhere and no complementary bottles of water in the room. Other than that, the beds were fantastic. The sheets were great. The pillows were awesome and the staff was terrific.
Reviewed on Jun 9, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,002, price is now $655 per person
$655
per person
Aug 17 - Aug 22
just found
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The excellent hotel launch our vacation in Chicago. The rooms were modern and comfortable. Did you help?
Reviewed on Jun 12, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,191, price is now $795 per person
$795
per person
Aug 17 - Aug 22
just found
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The bell hoppers were all very pleasant each and every time we left and came back inside!
Reviewed on May 16, 2026
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $1,319, price is now $842 per person
$842
per person
Jul 19 - Jul 25
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The two main complaints that I have is that there wasn’t a full length mirror anywhere and no complementary bottles of water in the room. Other than that, the beds were fantastic. The sheets were great. The pillows were awesome and the staff was terrific.
Reviewed on Jun 9, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,189, price is now $1,430 per person
$1,430
per person
Jul 19 - Jul 25
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The bell hoppers were all very pleasant each and every time we left and came back inside!
Reviewed on May 16, 2026
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $2,047, price is now $1,356 per person
$1,356
per person
Jul 19 - Jul 25
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The excellent hotel launch our vacation in Chicago. The rooms were modern and comfortable. Did you help?
Reviewed on Jun 12, 2026
Adventure hotels in Illinois
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
$209 nightly
The price is $248 total per night
$248 total
Jun 30 - Jul 1
Total with 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 luxury hotel include a conference center, a business center, and express check-in.
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
$203 nightly
The price is $241 total per night
$241 total
Jul 2 - Jul 3
Total with taxes and fees
At Hyatt Regency McCormick Place Chicago , guests have access to a gym, a sauna, and free WiFi in public areas. Valet parking is offered for USD 60 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, concierge services, and securing valuables. Additional amenities include meeting rooms, a conference center, and a 24-hour business center.
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
$221 nightly
The price is $263 total per night
$263 total
Jul 1 - Jul 2
Total with 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 92 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.
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 Illinois?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
JFK
John F. Kennedy Intl.
RFD
Greater Rockford
$186 Roundtrip, found 2 days ago
$186
Roundtrip
found 2 days ago
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$186 Roundtrip, found 1 day ago
$186
Roundtrip
found 1 day ago
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$195 Roundtrip, found 4 days ago
$195
Roundtrip
found 4 days ago
EWR
Newark Liberty Intl. Airport
STL
Lambert-St. Louis Intl.
$210 Roundtrip, found 21 hours ago
$210
Roundtrip
found 21 hours ago
JFK
John F. Kennedy Intl.
STL
Lambert-St. Louis Intl.
$227 Roundtrip, found 4 days ago
$227
Roundtrip
found 4 days ago
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