
Chicago Adventure Vacation Packages
Best Chicago Adventure packages
Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 6 - Aug 9
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) 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

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Fargo (FAR) 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

Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Fargo (FAR) 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
3 night Chicago 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
per person
Aug 6 - Aug 9
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) 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

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
New Orleans (MSY) 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

Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
per person
Sep 6 - Sep 9
found 1 day ago
Roundtrip flight included
Fargo (FAR) 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
4 night Chicago Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.

The Chicago Hotel Collection - Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Oct 8 - Oct 12
found 7 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, 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 elevator needs an upgrade, takes a long time to move up or down. Property is old
Reviewed on Jul 30, 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Sep 6 - Sep 10
found 18 hours ago
Roundtrip flight included
Denver (DEN) 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
Sep 6 - Sep 10
found 18 hours ago
Roundtrip flight included
Denver (DEN) 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
5 night Chicago Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.

Kinzie Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star 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.
Liked everything about this hotel and have stayed here a few times. Wish the gym was a little more up to date.
Reviewed on May 27, 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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

Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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
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 27
found 1 day ago
Roundtrip flight included
New York (NYC) 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

The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
per person
Sep 7 - Sep 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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
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
$232 nightly
The price is $272 total per night
$272 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.
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$60 Roundtrip, found 6 days ago
$60
Roundtrip
found 6 days ago
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, just found
$72
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$88 Roundtrip, found 5 days ago
$88
Roundtrip
found 5 days ago
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 2 hours ago
$96
Roundtrip
found 2 hours ago
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$100 Roundtrip, just found
$100
Roundtrip
just found
LGA
LaGuardia
MDW
Midway Intl.
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day 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