Chicago Adventure Vacation Packages
Best Chicago Adventure packages
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
Price was $638, price is now $448 per person
$448
per person
Oct 28 - Oct 31
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
I loved this place! For local everything was walking distance.
Reviewed on Sep 20, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $680, price is now $469 per person
$469
per person
Oct 28 - Oct 31
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
Room was nice & clean. Loved how convenient it was to CTA.
Reviewed on Sep 24, 2025
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
Price was $928, price is now $650 per person
$650
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Very nice stay in the downtown area
Great location and a lot of parking options around
Very good facility and very clean
Reviewed on Aug 22, 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
Price was $638, price is now $448 per person
$448
per person
Oct 28 - Oct 31
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
I loved this place! For local everything was walking distance.
Reviewed on Sep 20, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $680, price is now $469 per person
$469
per person
Oct 28 - Oct 31
found 11 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.
Room was nice & clean. Loved how convenient it was to CTA.
Reviewed on Sep 24, 2025
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
Price was $928, price is now $650 per person
$650
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Very nice stay in the downtown area
Great location and a lot of parking options around
Very good facility and very clean
Reviewed on Aug 22, 2025
4 night Chicago Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
Hotel Chicago Downtown, Autograph Collection by Marriott
Downtown Chicago
Save 100% on your flight
Price was $619, price is now $457 per person
$457
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Had a wonderful two nights stay. The staff were all extremely friendly and the room was very comfortable.
Reviewed on Jun 11, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $829, price is now $541 per person
$541
per person
Oct 28 - Nov 1
found 1 day 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.
Room was nice & clean. Loved how convenient it was to CTA.
Reviewed on Sep 24, 2025
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
Price was $755, price is now $552 per person
$552
per person
Oct 28 - Nov 1
found 1 day 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.
I loved this place! For local everything was walking distance.
Reviewed on Sep 20, 2025
5 night Chicago Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was $744, price is now $443 per person
$443
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
We received liked the service the staff provided, particularly Shanda.
Reviewed on Jul 20, 2025
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $854, price is now $556 per person
$556
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star luxury 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 Chicago Riverwalk are located nearby.
very beautiful and pleasant
Reviewed on Sep 20, 2025
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,253, price is now $817 per person
$817
per person
Oct 30 - Nov 4
found 18 hours ago
Roundtrip non-stop flight included
Guatemala City (GUA) to Chicago (ORD)
Stay at this 4.5-star 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.
All around a great location with incredible views. We stayed in a king suite on the 30th floor with views of both the city and lake thanks to architect that designed the building as a triangle that overlooks the Chicago river.
Reviewed on Sep 3, 2025
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was $1,308, price is now $835 per person
$835
per person
Nov 29 - Dec 6
found 1 day ago
Roundtrip flight included
Rochester (RST) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
We received liked the service the staff provided, particularly Shanda.
Reviewed on Jul 20, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,624, price is now $1,017 per person
$1,017
per person
Oct 29 - Nov 4
found 19 hours ago
Roundtrip non-stop flight included
Spokane (GEG) 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
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,913, price is now $1,914 per person
$1,914
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 5-star 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.
This is one of our best hotel experiences as a stay. Particularly impressed with the relaxed yet polished atmosphere of the hotel and engaging friendliness of the staff.
We had a poor experience at the flagship restaurant Shanghai Terrace however. Extremely hot and loud.
Reviewed on Feb 6, 2025
Adventure hotels in Chicago
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$241 nightly
The price is $278 total per night
$278 total
Oct 23 - Oct 24
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 securing valuables, access to locker space, 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
Free Cancellation
Reserve now, pay when you stay
$279 nightly
The price is $328 total per night
$328 total
Sep 25 - Sep 26
Total with 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 tours or tickets, dry cleaning/laundry, and luggage storage. 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
$319 nightly
The price is $374 total per night
$374 total
Oct 23 - Oct 24
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 87 per night. The 24-hour front desk has multilingual staff ready to assist with concierge services, dry cleaning/laundry, 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 Chicago?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LGA
LaGuardia
ORD
O'Hare Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, just found
$90
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$90 Roundtrip, found 5 hours ago
$90
Roundtrip
found 5 hours ago
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$92 Roundtrip, found 10 hours ago
$92
Roundtrip
found 10 hours ago
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
DAL
Love Field
ORD
O'Hare Intl.
$137 Roundtrip, found 6 hours ago
$137
Roundtrip
found 6 hours ago
DAL
Love Field
MDW
Midway Intl.
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
