Name: Cheerful 4 bedroom smart home w/ indoor fireplace
Address: Chicago

Plan a trip to see Barack Obama Residence

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

theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,216

per person

22 Dec - 27 Dec

found 1 day ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early! There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there. This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.

Reviewed on 10 Nov 2025

Arlo Chicago

Downtown Chicago

NZ$2,263

per person

22 Dec - 27 Dec

found 1 day ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.2/10 Wonderful! (1,852 reviews)

The room was really clean and the staff was very friendly and accommodating

Reviewed on 10 Nov 2025

Hilton Chicago O'Hare Airport

O'Hare

NZ$3,296

per person

21 Dec - 26 Dec

found 8 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

8.2/10 Very Good! (2,141 reviews)

Staff was great and the room was clean! We had to find a place for the night and didnt want to go far. It is convenient for that. Room rates are not too bad but the restaurant is a little pricey but still good food and service.

Reviewed on 9 Nov 2025

Tours & day trips

See all 153 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 48 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 9 activities

Chicago Perfume Making Classes on Magnificent Mile

Free cancellation available

Popular places to visit

Robie House

Witness the simple beauty of Frank Lloyd Wright’s designs in a Chicago house that epitomizes a popular American style of architecture.

Obama's House

Find out about the history of Chicago with a stop at Obama's House. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

KAM Synagogue

KAM Synagogue is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed theatre scene in this vibrant area.

Kam Isaiah Israel Congregation

You can find out about the history of Chicago when you stop by Kam Isaiah Israel Congregation. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Rainbow-PUSH Headquarters

Learn about the local history of Chicago when you take a trip to Rainbow-PUSH Headquarters. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

4944 S Woodlawn Ave

Find out about the history of Chicago with a stop at 4944 S Woodlawn Ave. Stroll along the lakeside or visit the notable monuments in this vibrant area.