
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
per person
Sep 8 - Sep 11
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) 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

Radisson Blu Aqua Hotel Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 9 - Sep 14
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
I mean, I love the property. The views are great and the amenities are endless. But the restaurant
Reviewed on Jul 15, 2025

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
per person
Sep 8 - Sep 11
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable.
The property is very nice, although we didn't get the two beds that we selected through Orbitz.
The hotel is on the red line, so not as convenient to the airport as a hotel on the blue line. Parking here is pricey.
If you stay here, Hendrickx Belgian Belgian Bread Crafter is around the corner and an absolute must visit. Wildberry is on the other side and also very good.
The Hancock Building is a two minute walk. If you love city views, the 360 experience is worth a visit, and is less crowded than the Willis Tower. We did the Tilt experience and it was not worth the money.
If you go to Chicago and haven't gone on an architectural boat tour, this is an absolute MUST. Be sure to choose a tour affiliated with the Chicago Architectural Center because that's a nonprofit worth supporting AND the guides are amazing. It's a 20 minute walk from the hotel and you walk along MichiganAve., which rivals Fifth Avenue in New York for window shopping, retail, artwork, and restaurants.
Love, love, love Chicago and would stay at this property again.
Reviewed on Jul 29, 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
Sep 8 - Sep 11
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) 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

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 12 - Oct 15
found 7 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

Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 12 - Oct 15
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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 Chicago Riverwalk 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.

Hilton Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 11 - Sep 15
just found
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4-star 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.
Good facility with convenient location.
Reviewed on Jul 27, 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 12
found 10 hours ago
Roundtrip flight included
Houston (HOU) 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

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 12
found 10 hours ago
Roundtrip flight included
Houston (HOU) 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
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
Sep 9 - Sep 14
found 7 hours ago
Roundtrip flight included
Los Angeles (LAX) 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

The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
per person
Oct 9 - Oct 14
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, 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

The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Miami (MIA) 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 vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.

Radisson Blu Aqua Hotel Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 20 - Sep 26
just found
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
I mean, I love the property. The views are great and the amenities are endless. But the restaurant
Reviewed on Jul 15, 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Sep 9 - Sep 15
found 5 hours ago
Roundtrip flight included
Houston (IAH) 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

The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
per person
Oct 9 - Oct 15
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, 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
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 luggage storage, securing valuables, and concierge services. 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
$235 nightly
The price is $276 total per night
$276 total
Sep 1 - Sep 2
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 securing valuables, 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 Chicago?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LGA
LaGuardia
ORD
O'Hare Intl.
$72 Roundtrip, just found
$72
Roundtrip
just found
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 6 hours ago
$72
Roundtrip
found 6 hours ago
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$88 Roundtrip, found 6 days ago
$88
Roundtrip
found 6 days ago
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$88 Roundtrip, found 6 days ago
$88
Roundtrip
found 6 days ago
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$90 Roundtrip, just found
$90
Roundtrip
just found
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$97 Roundtrip, just found
$97
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$100 Roundtrip, found 23 hours ago
$100
Roundtrip
found 23 hours ago
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$111 Roundtrip, found 6 days ago
$111
Roundtrip
found 6 days ago
LGA
LaGuardia
MDW
Midway Intl.
$145 Roundtrip, found 1 hour ago
$145
Roundtrip
found 1 hour ago
LAX
Los Angeles Intl.
MDW
Midway Intl.
$181 Roundtrip, found 7 hours ago
$181
Roundtrip
found 7 hours ago
LGA
LaGuardia
RFD
Greater Rockford
$208 Roundtrip, found 11 hours ago
$208
Roundtrip
found 11 hours 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