Chicago Vacations
Pack those stellar shades. We have Chicago vacation deals for you!
If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Chicago – great memories and a tall tale or two.
Hotwire can help you find your travel bliss with Chicago vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!
Pack everything you want – then take half of it out
We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.Bring comfortable walking shoes on your trip to Chicago
No one should have to endure walking tours in dress shoes or high heels. No one.Bring photocopies of your passport or license
You flew home from a great Chicago vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.Don’t underestimate the power of earplugs
Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.Always carry some cash
You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.Explore like a local
Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Chicago well.Chicago Flight + Hotel Packages
Fri, Jul 30 - Sun, Aug 1
Orlando Intl. - O'Hare Intl.
$408
The price now is $306 per personFlight + Hotel
Fri, Jul 9 - Sun, Jul 11
Logan Intl. - O'Hare Intl.
$807
The price now is $631 per personFlight + Hotel
Fri, Jul 30 - Mon, Aug 2
Logan Intl. - O'Hare Intl.
$1,184
The price now is $935 per personFlight + Hotel
Fri, Jul 30 - Tue, Aug 3
Orlando Intl. - O'Hare Intl.
$712
The price now is $566 per personFlight + Hotel
Fri, Jul 30 - Sun, Aug 1
Orlando Intl. - O'Hare Intl.
$525
The price now is $421 per personFlight + Hotel
Fri, Jul 9 - Sun, Jul 11
Logan Intl. - O'Hare Intl.
$489
The price now is $397 per personFlight + Hotel
Wed, Jul 7 - Sat, Jul 10
Minneapolis - St. Paul Intl. - O'Hare Intl.
$666
The price now is $550 per personFlight + Hotel
Fri, Jul 9 - Sun, Jul 11
Logan Intl. - O'Hare Intl.
$442
The price now is $371 per personFlight + Hotel
Thu, Jun 17 - Sun, Jun 20
Philadelphia Intl. - CHI-All Airports
$513
The price now is $431 per personFlight + Hotel
Fri, Jul 9 - Sun, Jul 11
Logan Intl. - O'Hare Intl.
$465
The price now is $400 per personFlight + Hotel
Fri, Jul 9 - Sun, Jul 11
Logan Intl. - O'Hare Intl.
$536
The price now is $467 per personFlight + Hotel
Fri, Jul 30 - Mon, Aug 2
Logan Intl. - O'Hare Intl.
$516
The price now is $456 per personFlight + Hotel
Chicago Vacation Packages 3-4 Night Stays
Fri, Jul 16 - Mon, Jul 19
Logan Intl. - O'Hare Intl.
$566
The price now is $420 per personFlight + Hotel
Fri, Jul 30 - Mon, Aug 2
Logan Intl. - O'Hare Intl.
$628
The price now is $488 per personFlight + Hotel
Fri, Jul 30 - Mon, Aug 2
Logan Intl. - O'Hare Intl.
$1,184
The price now is $935 per personFlight + Hotel
Fri, Jul 30 - Mon, Aug 2
Logan Intl. - O'Hare Intl.
$544
The price now is $431 per personFlight + Hotel
Fri, Jul 30 - Tue, Aug 3
Orlando Intl. - O'Hare Intl.
$712
The price now is $566 per personFlight + Hotel
Thu, Jul 8 - Sun, Jul 11
Minneapolis - St. Paul Intl. - O'Hare Intl.
$599
The price now is $480 per personFlight + Hotel
Fri, Jul 30 - Mon, Aug 2
Logan Intl. - O'Hare Intl.
$631
The price now is $511 per personFlight + Hotel
Wed, Jul 7 - Sat, Jul 10
Minneapolis - St. Paul Intl. - O'Hare Intl.
$666
The price now is $550 per personFlight + Hotel
Fri, Jul 30 - Mon, Aug 2
Logan Intl. - O'Hare Intl.
$628
The price now is $521 per personFlight + Hotel
Fri, Jul 30 - Mon, Aug 2
Logan Intl. - O'Hare Intl.
$581
The price now is $485 per personFlight + Hotel
Thu, Jun 17 - Sun, Jun 20
Philadelphia Intl. - CHI-All Airports
$513
The price now is $431 per personFlight + Hotel
Fri, Jul 30 - Mon, Aug 2
Logan Intl. - O'Hare Intl.
$668
The price now is $564 per personFlight + Hotel
Chicago Vacation Packages 5-7 Night Stays
Fri, Jun 25 - Wed, Jun 30
Minneapolis - St. Paul Intl. - O'Hare Intl.
$767
The price now is $566 per personFlight + Hotel
Fri, Jun 25 - Wed, Jun 30
Minneapolis - St. Paul Intl. - O'Hare Intl.
$710
The price now is $539 per personFlight + Hotel
Fri, Jun 25 - Wed, Jun 30
Minneapolis - St. Paul Intl. - O'Hare Intl.
$612
The price now is $473 per personFlight + Hotel
Sat, Jul 17 - Sat, Jul 24
Orlando Intl. - O'Hare Intl.
$973
The price now is $753 per personFlight + Hotel
Sat, Jul 17 - Sat, Jul 24
Orlando Intl. - O'Hare Intl.
$773
The price now is $616 per personFlight + Hotel
Fri, Jun 25 - Wed, Jun 30
Minneapolis - St. Paul Intl. - O'Hare Intl.
$527
The price now is $421 per personFlight + Hotel
Fri, Jun 25 - Wed, Jun 30
Minneapolis - St. Paul Intl. - O'Hare Intl.
$589
The price now is $477 per personFlight + Hotel
Fri, Jun 25 - Wed, Jun 30
Minneapolis - St. Paul Intl. - O'Hare Intl.
$703
The price now is $572 per personFlight + Hotel
Fri, Jun 25 - Wed, Jun 30
Minneapolis - St. Paul Intl. - O'Hare Intl.
$704
The price now is $575 per personFlight + Hotel
Sat, Jul 17 - Sat, Jul 24
Orlando Intl. - O'Hare Intl.
$588
The price now is $483 per personFlight + Hotel
Fri, Jun 25 - Wed, Jun 30
Minneapolis - St. Paul Intl. - O'Hare Intl.
$908
The price now is $748 per personFlight + Hotel
Sat, Jul 17 - Sat, Jul 24
Orlando Intl. - O'Hare Intl.
$606
The price now is $499 per personFlight + Hotel
Last Minute Hotel Deals in Chicago
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Frequently Asked Questions About Chicago
When is the best time of the year to find Chicago vacation package deals?
January is the best time to find cheap Chicago vacation deals.
When are the high and low seasons for Chicago vacations?
July, June, May are the busiest months for Chicago vacations, but October, December, November have the smallest crowds.
Where can I find the best last minute vacation deals for Chicago?
Only on Hotwire can you find last minute vacations from over Chicago destinations.
What if I have to cancel my trip to Chicago?
The fastest path to canceling your booking is through one of our self-serve tools found at https://vacation.hotwire.com/lp/coronavirus-travel
Book your Chicago Vacation
Other Hotels in Cities Near Chicago
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- Joliet Hotels
- Lombard Hotels
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Hotels in Neighborhoods Near Chicago
- Downtown Chicago Hotels
- Magnificent Mile Hotels
- The Loop Hotels
- River North Hotels
- Lincoln Park Hotels
- West Loop Hotels
- Lakeview Hotels
- Hyde Park Hotels
- Gold Coast Hotels
- South Loop Hotels
- Near North Side Hotels
- Wrigleyville Hotels
- Wicker Park Hotels
- Boystown Hotels
- Rogers Park Hotels
- Bronzeville Hotels
- Logan Square Hotels
- Chinatown Hotels
- Streeterville Hotels
- Uptown Hotels
Hotels Near Points of Interest in Chicago
- Hotels near Navy Pier
- Hotels near Wrigley Field
- Hotels near McCormick Place
- Hotels near Millennium Park
- Hotels near Union Station
- Hotels near Soldier Field
- Hotels near Willis Tower
- Hotels near Art Institute of Chicago
- Hotels near Naval Base Great Lakes
- Hotels near United Center
- Hotels near Grant Park
- Hotels near John G. Shedd Aquarium
- Hotels near Chicago Museum of Science and Industry
- Hotels near Chicago Theatre
- Hotels near Chicago Riverwalk
- Hotels near Field Museum of Natural History
- Hotels near Six Flags Great America
- Hotels near University of Chicago
- Hotels near Brookfield Zoo
- Hotels near Northwestern University