Illinois Adventure Vacation Packages
Best Illinois Adventure packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,141, price is now $788 per person
$788
per person
Jun 2 - Jun 5
found 2 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
Warwick Allerton - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,107, price is now $811 per person
$811
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The facility was lovely. Staff was kind BUT the bellman was rarely at his station. The area where our bags were kept were within eye sight BUT he was never there to take or give bags promptly. He was hopefully busy doing other things for staff and guests but this was a downside of our stay.
Reviewed on Jan 5, 2026
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,545, price is now $1,913 per person
$1,913
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
3 night Illinois Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Warwick Allerton - Chicago
Downtown Chicago
Price was $510, price is now $373 per person
$373
per person
Jul 5 - Jul 8
found 4 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The facility was lovely. Staff was kind BUT the bellman was rarely at his station. The area where our bags were kept were within eye sight BUT he was never there to take or give bags promptly. He was hopefully busy doing other things for staff and guests but this was a downside of our stay.
Reviewed on Jan 5, 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $632, price is now $397 per person
$397
per person
Jul 3 - Jul 6
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,368, price is now $870 per person
$870
per person
Jun 3 - Jun 6
found 3 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Room was clean and comfortable. We really appreciated the chocolates and water!
Reviewed on Feb 25, 2026
4 night Illinois Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
Warwick Allerton - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,107, price is now $811 per person
$811
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The facility was lovely. Staff was kind BUT the bellman was rarely at his station. The area where our bags were kept were within eye sight BUT he was never there to take or give bags promptly. He was hopefully busy doing other things for staff and guests but this was a downside of our stay.
Reviewed on Jan 5, 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,452, price is now $823 per person
$823
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,355, price is now $887 per person
$887
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
Amazing view!! Great rooftop at night!!! Drinks were excellent Expresso Martini!!
Reviewed on Mar 30, 2026
5 night Illinois Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
Sofitel Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,009, price is now $728 per person
$728
per person
Jul 6 - Jul 11
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Great location, friendly staff, nice clean rooms.
Reviewed on Feb 1, 2026
Swissotel - Chicago
Downtown Chicago
Price was $2,300, price is now $1,194 per person
$1,194
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,957, price is now $1,233 per person
$1,233
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Amazing view!! Great rooftop at night!!! Drinks were excellent Expresso Martini!!
Reviewed on Mar 30, 2026
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
Price was $1,024, price is now $702 per person
$702
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this 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.
The room smelled and the awful noise from the bathroom exhaust fan was annoying.
Reviewed on Mar 2, 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,966, price is now $1,665 per person
$1,665
per person
Jun 2 - Jun 8
found 23 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,279, price is now $1,524 per person
$1,524
per person
Jun 2 - Jun 8
found 23 hours ago
Roundtrip flight included
Charlotte (CLT) 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.
Amazing view!! Great rooftop at night!!! Drinks were excellent Expresso Martini!!
Reviewed on Mar 30, 2026
Adventure hotels in Illinois
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$168 nightly
The price is $195 total per night
$195 total
May 25 - May 26
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 concierge services, dry cleaning/laundry, and access to locker space. Other amenities at this luxury 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
$198 nightly
The price is $235 total per night
$235 total
May 25 - May 26
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 luggage storage, concierge services, and dry cleaning/laundry. Additional amenities include meeting rooms, a conference center, and a 24-hour business center.
Free WiFi
Restaurant
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$246 nightly
The price is $292 total per night
$292 total
May 25 - May 26
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 luggage storage. 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 Illinois?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
DFW
Dallas-Fort Worth Intl.
STL
Lambert-St. Louis Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$89 Roundtrip, found 6 hours ago
$89
Roundtrip
found 6 hours ago
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 5 days ago
$98
Roundtrip
found 5 days ago
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$129 Roundtrip, found 21 hours ago
$129
Roundtrip
found 21 hours ago
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$176 Roundtrip, just found
$176
Roundtrip
just found
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$178 Roundtrip, found 5 days ago
$178
Roundtrip
found 5 days ago
DAL
Love Field
ORD
O'Hare Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
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