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

Pendry Chicago

Downtown Chicago

per person

18 Sept - 22 Sept

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,033 reviews)

We enjoyed the rooftop dining--the view is terrific, especially after dark. Excellent location on Michigan Ave near restaurants, shopping and museums. Did the valet parking and it worked well for us. The service was all around excellent including checkin/checkout, in room dining service (we did breakfast), concierge, baggage help and valet . They were able to give us a late check out so we could fit in an architectural boat tour and then kept our luggage all day until evening so we could squeeze more out of this long weekend trip to the Windy City. The hotel is clean, stylish and service is top rate. I would highly recommend this hotel.

Reviewed on 11 Aug 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

18 Sept - 22 Sept

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.4/10 Exceptional! (1,679 reviews)

Amazing property well worth the money

Reviewed on 11 Aug 2025

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

18 Sept - 22 Sept

found 1 day ago

Return direct flight included

Dublin (DUB) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Tours & day trips

See all 177 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 35 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 32 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

Cloud Gate

4.5/5(3 reviews)

You can learn about the history of Chicago with a visit to Cloud Gate. Discover the entertainment choices and notable monuments in this vibrant area.

Marshall Field Building

You can learn about the history of Chicago with a trip to Marshall Field Building. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Crown Fountain

Innovative and certainly unique, this art installation in Millennium Park features the faces of 1,000 Chicagoans blown up five stories tall.

Pritzker Pavilion

Free concerts and Frank Gehry’s characteristic forms are some of the attractions of this modern performance venue in Chicago’s Millennium Park.

State Street

During your visit to Chicago, you can find the perfect gifts to bring home at State Street. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.