Illinois Adventure Vacation Packages

Best Illinois Adventure packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $926, price is now $699 per person
$699
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Baltimore (BWI) 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.
The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District.

Reviewed on Jul 28, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $3,271, price is now $2,261 per person
$2,261
per person
Aug 2 - Aug 5
found 24 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Downtown Chicago
Price was $1,318, price is now $1,026 per person
$1,026
per person
Aug 1 - Aug 4
found 6 hours ago
Roundtrip flight included
New York (NYC) 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.
Hotel 55 was close to everything walking distance to stores restaurants the service was wonderful that would be my go-to hotel for now on if I ever stay downtown to Chicago

Reviewed on Jul 29, 2026

3 night Illinois Adventure vacation packages with airfare

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $779, price is now $526 per person
$526
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $3,271, price is now $2,261 per person
$2,261
per person
Aug 2 - Aug 5
found 24 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,321, price is now $997 per person
$997
per person
Oct 2 - Oct 5
just found
Roundtrip flight included
Austin (AUS) 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.
The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District.

Reviewed on Jul 28, 2026

4 night Illinois Adventure vacation packages with flight

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $917, price is now $668 per person
$668
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,231, price is now $872 per person
$872
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,922, price is now $1,427 per person
$1,427
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.

5 night Illinois Adventure vacation packages with airfare included

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,110, price is now $798 per person
$798
per person
Oct 2 - Oct 7
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Lovely clean hotel, centrally Located and very helpful staff.

Reviewed on Jul 28, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,969, price is now $1,995 per person
$1,995
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (ORL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,652, price is now $1,115 per person
$1,115
per person
Oct 2 - Oct 7
found 17 hours ago
Roundtrip flight included
Boston (BOS) 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.

Adventure vacation packages for 6-7 nights

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was $1,543, price is now $1,073 per person
$1,073
per person
Oct 2 - Oct 9
found 16 hours ago
Roundtrip non-stop flight included
McAllen (MFE) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $2,495, price is now $1,664 per person
$1,664
per person
Oct 2 - Oct 9
found 16 hours ago
Roundtrip non-stop flight included
McAllen (MFE) 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.

Adventure hotels in Illinois

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$249 nightly
The price is $297 total per night
$297 total
Aug 9 - Aug 10
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, luggage storage, and dry cleaning/laundry. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$237 nightly
The price is $281 total per night
$281 total
Aug 10 - Aug 11
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 luggage storage, securing valuables, and concierge services. Additional amenities include meeting rooms, a conference center, and a 24-hour business center.
Free WiFi
Restaurant
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$280 nightly
The price is $333 total per night
$333 total
Aug 23 - Aug 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 92 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
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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.

Wed, Oct 14 - Tue, Oct 20
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$82 Roundtrip, found 22 hours ago
$82
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Denver Intl. to Lambert-St. Louis Intl., returning Tue, Oct 20, priced at $82 found 22 hours ago
Thu, Oct 29 - Sun, Nov 1
DEN
Denver Intl.
PIA
Greater Peoria Regional
$95 Roundtrip, just found
$95
Roundtrip
just found
Select Allegiant Air flight, departing Thu, Oct 29 from Denver Intl. to Greater Peoria Regional, returning Sun, Nov 1, priced at $95 just found
Sat, Sep 5 - Wed, Sep 9
DEN
Denver Intl.
ORD
O'Hare Intl.
$116 Roundtrip, found 3 hours ago
$116
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Denver Intl. to O'Hare Intl., returning Wed, Sep 9, priced at $116 found 3 hours ago
Wed, Sep 23 - Wed, Sep 30
SMF
Sacramento Intl.
STL
Lambert-St. Louis Intl.
$137 Roundtrip, found 2 hours ago
$137
Roundtrip
found 2 hours ago
Select Alaska Airlines flight, departing Wed, Sep 23 from Sacramento Intl. to Lambert-St. Louis Intl., returning Wed, Sep 30, priced at $137 found 2 hours ago
Thu, Dec 3 - Mon, Dec 7
DEN
Denver Intl.
MDW
Midway Intl.
$205 Roundtrip, found 5 days ago
$205
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Dec 3 from Denver Intl. to Midway Intl., returning Mon, Dec 7, priced at $205 found 5 days ago
Mon, Aug 31 - Tue, Sep 1
DEN
Denver Intl.
RFD
Greater Rockford
$212 Roundtrip, found 11 hours ago
$212
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Mon, Aug 31 from Denver Intl. to Greater Rockford, returning Tue, Sep 1, priced at $212 found 11 hours ago
Sun, Aug 30 - Tue, Sep 1
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$218 Roundtrip, found 21 hours ago
$218
Roundtrip
found 21 hours ago
Select Delta flight, departing Sun, Aug 30 from John F. Kennedy Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $218 found 21 hours ago
Thu, Sep 10 - Sat, Sep 12
JFK
John F. Kennedy Intl.
RFD
Greater Rockford
$226 Roundtrip, found 2 days ago
$226
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Sep 10 from John F. Kennedy Intl. to Greater Rockford, returning Sat, Sep 12, priced at $226 found 2 days ago
Sat, Sep 26 - Wed, Sep 30
SMF
Sacramento Intl.
ORD
O'Hare Intl.
$272 Roundtrip, found 12 hours ago
$272
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Sacramento Intl. to O'Hare Intl., returning Wed, Sep 30, priced at $272 found 12 hours ago
Thu, Oct 1 - Mon, Oct 5
JFK
John F. Kennedy Intl.
MDW
Midway Intl.
$295 Roundtrip, found 2 days ago
$295
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Oct 1 from John F. Kennedy Intl. to Midway Intl., returning Mon, Oct 5, priced at $295 found 2 days ago
Thu, Sep 10 - Fri, Sep 11
JFK
John F. Kennedy Intl.
MLI
Quad City Intl.
$304 Roundtrip, found 2 days ago
$304
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Sep 10 from John F. Kennedy Intl. to Quad City Intl., returning Fri, Sep 11, priced at $304 found 2 days ago
Wed, Nov 4 - Mon, Nov 9
JFK
John F. Kennedy Intl.
STL
Lambert-St. Louis Intl.
$313 Roundtrip, found 19 hours ago
$313
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Wed, Nov 4 from John F. Kennedy Intl. to Lambert-St. Louis Intl., returning Mon, Nov 9, priced at $313 found 19 hours ago
Mon, Nov 2 - Sat, Nov 7
JFK
John F. Kennedy Intl.
BMI
Central Illinois Regional
$400 Roundtrip, found 3 days ago
$400
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Nov 2 from John F. Kennedy Intl. to Central Illinois Regional, returning Sat, Nov 7, priced at $400 found 3 days ago
Fri, Aug 7 - Sun, Aug 9
JFK
John F. Kennedy Intl.
CMI
University Of Illinois Urbana-Champaign Williard
$439 Roundtrip, found 4 days ago
$439
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Aug 7 from John F. Kennedy Intl. to University Of Illinois Urbana-Champaign Williard, returning Sun, Aug 9, priced at $439 found 4 days ago

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