86 deals from our U.S. site*
* Taxes and fees may be additional.
Source: Trump International Hotel & Tower Chicago

Luxuriate at a 5-star downtown hotel with show-stopping views and a long list of awards, including 'World's Best'

Select dates through July 8
Source: Major Airlines on Fly.com

Fly from Tampa, Chicago, Louisville and more

Travel into July
Source: CheapCaribbean.com

Spend three nights at the Condado Plaza Hilton and receive an upgrade to an ocean view room.

Select departures May 3-6; Aug. 24 - Oct. 31
Source: Vacation Express

Stay at the Omni Cancun, which boasts a swim-up sushi bar, three oceanfront pools, turtle release program and more

Select departures, May-September
Source: The Westin Michigan Avenue

Snag a room at a AAA 4-Diamond hotel on Chicago's world-famous Magnificent Mile.

Select dates through July 3
Source: The Westin Chicago River North

Check in to a AAA 4-Diamond hotel with a top location and sweeping views of the Chicago river.

Select dates through Aug. 29
Source: Hilton Chicago O'Hare

Make flying into and out of the Windy City a breeze with this bed & breakfast package

Weekends in May; +$20 weekends in April
Source: Hotel Lincoln

Take on Chicago like a local at a boutique 4-star hotel, located in the city's posh Lincoln Park neighborhood.

Most Sundays-Thursdays through Aug. 27
Source: 'Chicago The Musical' on Broadway

Save up to $50 on the Tony- and Grammy award-winning tale of fame, fortune and "All That Jazz."

Through June 29
Source: 'Cuff Me!'

Tickets are more than 60% off for the musical comedy "Cuff Me!"

Through April 26
Source: Major Airlines on Fly.com

Fly from Boston, Chicago, San Francisco & more

Into July
Source: Major Airlines on Fly.com

Fly from San Francisco, Los Angeles, Chicago & more

Into July
Source: Major Airlines on Fly.com

Fly from NYC, Los Angeles, Chicago & more

Into July
Source: 'Rose and the Rime'

"Rose and the Rime" opens this month in the Carnival Studio Theater

April 23, 24 & 26
Source: The Apartment

"Girls Night: The Musical" follows five friends during a wild and outrageous night out, and subscribers can save up to 60% on tickets.

Select dates May 2 - June 14
Source: Bottlenotes

Swirl & sip wines from California, Spain, France, Italy, New Zealand and Brazil during "Around the World in 80 Sips" at the Museum of Contemporary Art

Friday, May 9
Source: Hertz

Hit the open road with car rentals in cities from coast to coast

Through April
Source: Lyceum Theatre

Save 25% on tickets to this "convulsively funny" show (Variety).

April 23 - May 25
Source: 'Defending the Caveman'

This long-running comedy comes to the City Theatre, and tickets are 45% off.

May 15-25
Source: Bottlenotes

Swirl, sip and savor international wines during the tasting event "Around the World in 80 Sips" at the Museum of Contemporary Art in Chicago, and save 50% on tickets.

April 17, 2014 - May 8, 2014
Need to make travel arrangements?
Compare Multiple Travel Sites in One Search
From: To: Travelers:
Depart: Return: One-way
Enter city: Guests:
Check-in: Check-out: Rooms:
From: To: Travelers:
Depart: Return: Rooms:
Enter city: Pick-up Time:
Pick-up Date: Return Date: Return Time:

Compare Hotel Rates

Travelzoo Tips

Andrew Young — Travel, Entertainment and Local Deal Expert
Andrew Young
Deal Expert, New York
Summer is coming. Our thoughts turn to beaches, grilling meats and summer vacation. More