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 $661, price is now $491 per person
$491
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
Price was $886, price is now $658 per person
$658
per person
Sep 26 - Sep 29
found 16 hours ago
Roundtrip non-stop 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
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,118, price is now $861 per person
$861
per person
Sep 26 - Sep 29
found 16 hours ago
Roundtrip non-stop 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
3 night Chicago Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Warwick Allerton - Chicago
Downtown Chicago
Price was $508, price is now $374 per person
$374
per person
Oct 28 - Oct 31
found 11 hours ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star family-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.
I love the location and I got a great deal. It's not the most updated inside their rooms, but it was not a deal breaker either. I wished their bar was open during the week though.
Reviewed on Sep 11, 2025
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
Price was $886, price is now $658 per person
$658
per person
Sep 26 - Sep 29
found 16 hours ago
Roundtrip non-stop 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
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
Price was $661, price is now $491 per person
$491
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
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
Price was $599, price is now $411 per person
$411
per person
Nov 27 - Dec 1
found 11 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Nice, clean hotel, friendly staff, very comfortable room, within walking distance from lake Michigan, major attractions, shopping and dining.
Reviewed on Sep 5, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Price was $829, price is now $559 per person
$559
per person
Oct 27 - Oct 31
found 11 hours 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.
Property is awesome, this should be a 4 star hotel, the room was amazing. Sadly, the staff has a really bad attitude, they are despicable, slow and don't give the information you need.
Reviewed on Sep 18, 2025
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
Price was $1,186, price is now $838 per person
$838
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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
5 night Chicago Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $782, price is now $531 per person
$531
per person
Oct 27 - Nov 1
found 24 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Generous breakfast, beautiful room. Convenient to go everywhere.
Reviewed on Sep 3, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $914, price is now $600 per person
$600
per person
Dec 7 - Dec 12
found 3 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 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 Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,074, price is now $720 per person
$720
per person
Oct 27 - Nov 1
found 24 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) 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.
Property is awesome, this should be a 4 star hotel, the room was amazing. Sadly, the staff has a really bad attitude, they are despicable, slow and don't give the information you need.
Reviewed on Sep 18, 2025
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
Sofitel Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $832, price is now $579 per person
$579
per person
Dec 8 - Dec 15
found 4 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Centrally located offered early check in luxury toiletries the most comfy bed ever it smells luxurious
The cleaning staff went above and beyond overall excellent there were some issues with the online service menu for dining and amenities and the facilities can use some attention when it comes to chipping paint and other small aesthetic details but otherwise fabulous
Reviewed on Jul 8, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,632, price is now $1,848 per person
$1,848
per person
Sep 26 - Oct 2
found 8 hours ago
Roundtrip non-stop flight included
Seattle (SEA) 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.
Great location, wonderful views and attentive staff made this an enjoyable stay. Super convenient for enjoying the sites of an amazing city.
Reviewed on Sep 16, 2025
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
Price was $1,823, price is now $1,296 per person
$1,296
per person
Sep 26 - Oct 2
found 8 hours ago
Roundtrip non-stop flight included
Seattle (SEA) 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
Adventure hotels in Chicago
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$258 nightly
The price is $298 total per night
$298 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 22 - Oct 23
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.
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$49 Roundtrip, found 4 days ago
$49
Roundtrip
found 4 days ago
LGA
LaGuardia
ORD
O'Hare Intl.
$76 Roundtrip, just found
$76
Roundtrip
just found
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$89 Roundtrip, found 4 days ago
$89
Roundtrip
found 4 days ago
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$91 Roundtrip, found 2 hours ago
$91
Roundtrip
found 2 hours ago
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 5 days ago
$94
Roundtrip
found 5 days ago
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$99 Roundtrip, found 1 hour ago
$99
Roundtrip
found 1 hour ago
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$105 Roundtrip, found 6 days ago
$105
Roundtrip
found 6 days ago
IAH
George Bush Intercontinental
MDW
Midway Intl.
$110 Roundtrip, found 3 hours ago
$110
Roundtrip
found 3 hours ago
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$126 Roundtrip, just found
$126
Roundtrip
just found
BWI
Baltimore Washington Intl. Thurgood Marshall
RFD
Greater Rockford
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
IAH
George Bush Intercontinental
RFD
Greater Rockford
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$162 Roundtrip, just found
$162
Roundtrip
just found
PAE
Seattle Paine Field Intl. Airport
ORD
O'Hare Intl.
$162 Roundtrip, just found
$162
Roundtrip
just found
LAX
Los Angeles Intl.
MDW
Midway Intl.
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
