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Chicago Vacation Packages

Cheap Chicago Vacation Packages

You’re on the hunt for a steal of a deal on your Chicago vacation package. You’ve got your list of things you want, and you’re checking it twice: a ballin’ (on a budget) Chicago hotel, a champagne poppin’ flight (for a knock-off beer price), and maybe even a super-nice car rental (for a borrowed bike fee).

Think it’s all just a dream? Not when you book your Chicago vacation deal with Hotwire.

Are you for real with these vacation package deals

Daydreaming is even better when wildly good deals become your reality. Scoring hotel and flight deals to Chicago for a price that works with your budget is realer than real when you book your package with Hotwire. Ready to get all of your wildest dreams fulfilled (for way less than you expected)? Don’t sleep on these Hotwire deals.

Frequently Asked Questions About Vacation Packages

How much is a vacation to Chicago?

When you want to book the very best Chicago getaway, but you aren’t looking to empty your bank account on planning your trip, cheap vacation packages are the way to go. You can jump into an incredible vacay to Chicago for as low as $246 and keep your cash for the necessities—like the dreamiest fun times in town.

When is the best time to book a vacation package to Chicago?

Looking to save some extra cash on your Chicago vacation? Try going on your getaway in October, December, November, which is the off-season, and avoid the most popular time to vacation in the month of July, June, May. Want to get away now-ish and still save? Book a last-minute vacation package with a Hot Rate hotel deal. You could save up to 60% off on your hotel versus booking a listed rate two weeks earlier.

How to get the best vacation package deals to Chicago?

If scoring the very best deal on your Chicago vacation is at the top of your to-do list, book your package with Hotwire and prepare to get way more bang for your buck.

What is the cheapest day to book a vacation package?

Reserving a Chicago vacation package on a Tuesday is the cheapest day to book, or you can save more any day on Hotwire, with packages as low as $246.

Can I vacation in Chicago right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Chicago right now?” When it’s time to book your vacation package, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

What does Hotwire Chicago travel package include?

When you book a package deal on Hotwire, you can expect a Chicago vacation package with airfare and hotel. Want a rental car too? No biggie‚ you can add it to your package. Everything you need for an amazing trip? Check.

Chicago Flight + Hotel Packages

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Price was $561, price is now $408 per person
per person
Dec 17 - Dec 21
Roundtrip flight included
Greenville (GSP) to Chicago (ORD)
Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk and Michigan Avenue. Grant Park and Harris Theater are also within 10 minutes. Millennium Station is 10 minutes by foot and State Station is 11 minutes.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Save 100% on your flightPrice was $1,012, price is now $737 per person
per person
Dec 29 - Jan 3
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk, Michigan Avenue, and Grant Park. Harris Theater and Chicago Theatre are also within 10 minutes. Randolph-Wabash Station is 7 minutes by foot and State Station is 7 minutes.
Lincolnshire Marriott Resort

Lincolnshire Marriott Resort

4 out of 5
Price was $846, price is now $648 per person
per person
Dec 25 - Jan 1
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
Situated in Lincolnshire, this golf resort is 2.8 mi (4.6 km) from Chevy Chase Country Club and 2.9 mi (4.6 km) from Trinity International University. Northwestern Medicine and Cuneo Mansion and Gardens are also within 6 mi (10 km).
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Price was $612, price is now $471 per person
per person
Dec 17 - Dec 21
Roundtrip flight included
Greenville (GSP) to Chicago (ORD)
This family-friendly Chicago hotel is located in the historical district, just steps from Grant Park and Aon Center. Michigan Avenue and Chicago Riverwalk are also within 5 minutes. Randolph-Wabash Station is 8 minutes by foot and State Station is 8 minutes.
Sheraton Grand Chicago

Sheraton Grand Chicago

4 out of 5
Price was $595, price is now $467 per person
per person
Dec 17 - Dec 21
Roundtrip flight included
Greenville (GSP) to Chicago (ORD)
Located in Near North Side, this hotel is within a 15-minute walk of Michigan Avenue and Navy Pier. Millennium Park and John Hancock Center are also within 1 mi (2 km). Grand Station (Red Line) is 11 minutes by foot and Randolph-Wabash Station is 13 minutes.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Price was $758, price is now $595 per person
per person
Dec 17 - Dec 21
Roundtrip flight included
Greenville (GSP) to Chicago (ORD)
Located in River North, this luxury hotel is within a 5-minute walk of Michigan Avenue and State Street. Wrigley Building and Northwestern Memorial Hospital are also within 10 minutes. Grand Station (Red Line) is only a 3-minute walk and Chicago Station (Red Line) is 10 minutes.
The Langham, Chicago

The Langham, Chicago

5 out of 5
Save 100% on your flightPrice was $1,290, price is now $1,022 per person
per person
Dec 17 - Dec 21
Roundtrip flight included
Greenville (GSP) to Chicago (ORD)
This family-friendly Chicago hotel is located in the entertainment district, within a 15-minute walk of Michigan Avenue, Millennium Park, and Art Institute of Chicago. John Hancock Center and Navy Pier are also within 1 mi (2 km). State Station is 5 minutes by foot and Randolph-Wabash Station is 6 minutes.
Courtyard by Marriott Chicago Downtown River North

Courtyard by Marriott Chicago Downtown River North

3 out of 5
Price was $309, price is now $246 per person
per person
Dec 2 - Dec 5
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Located in River North, this hotel is within a 5-minute walk of State Street, Wrigley Building, and Michigan Avenue. House of Blues Chicago and Chicago Theatre are also within 10 minutes. Grand Station (Red Line) is only a 3-minute walk and State Station is 6 minutes.

Chicago Vacation Packages 3-4 Night Stays

Fairmont Chicago at Millennium Park Gold Experience
4.5-star property

Fairmont Chicago at Millennium Park Gold Experience

The Loop

Nov 26 - Nov 29

1 night stay

Washington (DCA) to Chicago (ORD)

United • Roundtrip • Coach
Price was $994, price is now $721 per person
per person
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

Lakeshore East

Jan 11 - Jan 14

1 night stay

Washington (DCA) to Chicago (ORD)

Roundtrip • Coach
Price was $450, price is now $344 per person
per person
Sheraton Grand Chicago
4.0-star property

Sheraton Grand Chicago

Streeterville

Jan 11 - Jan 14

1 night stay

Washington (DCA) to Chicago (ORD)

Roundtrip • Coach
Price was $418, price is now $347 per person
per person
Thompson Chicago
4.5-star property

Thompson Chicago

Rush and Division

Nov 26 - Nov 29

1 night stay

Washington (DCA) to Chicago (ORD)

United • Roundtrip • Coach
Price was $880, price is now $737 per person
per person

Last Minute Hotel Deals in Chicago

Hot Rate® Hotel

3.5-star Hotel in Millennium Park
3.5 out of 5

3.5-star Hotel

in Millennium Park
0.3 miles from Chicago
31% off
Price was $138 per night and is now $95 per night
3.5-star Hotel in Millennium Park

Hot Rate® Hotel

3.5-star Hotel in Millennium Park
3.5 out of 5

3.5-star Hotel

in Millennium Park
0.3 miles from Chicago
30% off
Price was $141 per night and is now $99 per night
3.5-star Hotel in Millennium Park

Hot Rate® Hotel

3.5-star Hotel in Theater District - Loop
3.5 out of 5

3.5-star Hotel

in Theater District - Loop
0.2 miles from Chicago
41% off
Price was $169 per night and is now $100 per night
3.5-star Hotel in Theater District - Loop

Hot Rate® Hotel

3.5-star Hotel in Millennium Park
3.5 out of 5

3.5-star Hotel

in Millennium Park
0.3 miles from Chicago
29% off
Price was $154 per night and is now $109 per night
3.5-star Hotel in Millennium Park

Hot Rate® Hotel

3.5-star Hotel in River North
3.5 out of 5

3.5-star Hotel

in River North
0.8 miles from Chicago
28% off
Price was $151 per night and is now $109 per night
3.5-star Hotel in River North

Hot Rate® Hotel

3.5-star Hotel in River North
3.5 out of 5

3.5-star Hotel

in River North
0.8 miles from Chicago
22% off
Price was $144 per night and is now $112 per night
3.5-star Hotel in River North

Hot Rate® Hotel

3.5-star Hotel in Millennium Park
3.5 out of 5

3.5-star Hotel

in Millennium Park
0.3 miles from Chicago
29% off
Price was $161 per night and is now $114 per night
3.5-star Hotel in Millennium Park

Hot Rate® Hotel

3.5-star Hotel in Theater District - Loop
3.5 out of 5

3.5-star Hotel

in Theater District - Loop
0.2 miles from Chicago
42% off
Price was $198 per night and is now $115 per night
3.5-star Hotel in Theater District - Loop
Show all deals

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Thu, Dec 9 - Tue, Jan 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$57
Spirit Airlines
Spirit Airlines
Fri, Jan 7 - Sat, Jan 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$59
Spirit Airlines
Spirit Airlines
Sat, Dec 4 - Sat, Dec 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$61
Spirit Airlines
Spirit Airlines
Sat, Nov 13 - Sat, Dec 4
EWR
Liberty Intl.
ORD
O'Hare Intl.
$75
Spirit Airlines

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