Illinois Adventure Vacation Packages
Best Illinois Adventure packages
Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel
Downtown Chicago
Price was $646, price is now $515 per person
$515
per person
Jun 30 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,815, price is now $1,430 per person
$1,430
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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
The Ritz-Carlton, Chicago
Downtown Chicago
Price was $1,223, price is now $979 per person
$979
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Fresno (FAT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Best place in the city of Chicago to stay at
Reviewed on Dec 1, 2024
3 night Illinois Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $844, price is now $609 per person
$609
per person
Jul 2 - Jul 5
found 8 hours ago
Roundtrip flight included
Boston (BOS) 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
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,276, price is now $873 per person
$873
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Hilton Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,537, price is now $1,200 per person
$1,200
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Excellent location; excellent staff throughout all services of the hotel. Very nice gym, albeit for a daily fee - nice sized lane pool and jacuzzis.
Reviewed on May 26, 2026
4 night Illinois Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,696, price is now $1,000 per person
$1,000
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $2,274, price is now $1,624 per person
$1,624
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Knoxville (TYS) 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
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,421, price is now $1,044 per person
$1,044
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this business-friendly 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.
Room design, checking nd check out experience, general cleanliness etc
Reviewed on Feb 10, 2026
5 night Illinois 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
Price was $1,072, price is now $760 per person
$760
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,190, price is now $1,181 per person
$1,181
per person
Jul 31 - Aug 5
found 3 hours ago
Roundtrip flight included
Chattanooga (CHA) 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
Hotel 55 Chicago Downtown
Downtown Chicago
Save 100% on your flight
Price was $1,416, price is now $993 per person
$993
per person
Jul 31 - Aug 5
found 3 hours ago
Roundtrip flight included
Chattanooga (CHA) 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
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,415, price is now $1,283 per person
$1,283
per person
Aug 1 - Aug 7
found 1 hour ago
Roundtrip non-stop 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 $2,148, price is now $1,347 per person
$1,347
per person
Aug 1 - Aug 7
found 1 hour ago
Roundtrip non-stop 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.
The bell hoppers were all very pleasant each and every time we left and came back inside!
Reviewed on May 16, 2026
Kinzie Hotel
Downtown Chicago
Save 100% on your flight
Price was $2,108, price is now $1,445 per person
$1,445
per person
Jun 24 - Jun 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Adventure hotels in Illinois
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$315 nightly
The price is $375 total per night
$375 total
Jun 21 - Jun 22
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, securing valuables, and luggage storage. 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
$324 nightly
The price is $385 total per night
$385 total
Jun 7 - Jun 8
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 securing valuables, dry cleaning/laundry, and tours or tickets. 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
$331 nightly
The price is $394 total per night
$394 total
Jun 21 - Jun 22
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 tours or tickets, luggage storage, and dry cleaning/laundry. 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.
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$172 Roundtrip, just found
$172
Roundtrip
just found
JFK
John F. Kennedy Intl.
RFD
Greater Rockford
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$177 Roundtrip, found 1 hour ago
$177
Roundtrip
found 1 hour ago
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$180 Roundtrip, found 6 days ago
$180
Roundtrip
found 6 days ago
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
EWR
Newark Liberty Intl. Airport
STL
Lambert-St. Louis Intl.
$230 Roundtrip, found 1 day ago
$230
Roundtrip
found 1 day ago
EWR
Newark Liberty Intl. Airport
MLI
Quad City Intl.
$281 Roundtrip, found 3 days ago
$281
Roundtrip
found 3 days ago
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