Downtown Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Indoor pool
    Aug 2 - Aug 6

    Palmer House a Hilton Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,456 reviews)
    "Old style luxury hotel doesn’t disappoint. Great food, friendly staff and comfortable rooms. "
    Reviewed May 16, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥408,051
    ￥365,771
    per traveler
    found 9 hours ago
    Palmer House a Hilton Hotel
  • Smart TV
    Aug 2 - Aug 6

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (481 reviews)
    "Yes"
    Reviewed May 12, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥499,829
    ￥395,707
    per traveler
    found 8 hours ago
    Level Chicago Fulton Market
  • Terrace/patio
    Aug 2 - Aug 6

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,506 reviews)
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥492,976
    ￥399,941
    per traveler
    found 9 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Lunch and dinner served
    Aug 2 - Aug 6

    Radisson Blu Aqua Hotel Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    8.6/10 - Excellent (1,946 reviews)
    "Bellhop Hasan was so great!"
    Reviewed May 19, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥440,415
    ￥389,231
    per traveler
    found 9 hours ago
    Radisson Blu Aqua Hotel Chicago
  • Interior detail
    Aug 2 - Aug 6

    Staypineapple, An Iconic Hotel, The Loop + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (1,072 reviews)
    "Clean rooms, comfy bed."
    Reviewed May 17, 2026
    Roundtrip • Tokyo (NRT) - Chicago (ORD)
    NRT - ORD • 1 stop ORD - NRT • 1 stop
    ￥450,796
    ￥399,952
    per traveler
    found 9 hours ago
    Staypineapple, An Iconic Hotel, The Loop

Where to stay in Downtown

Find the best Downtown areas and neighborhoods for the activities you enjoy most. Learn more about Downtown
Scenic fall foliage along Black river in Michigan upper peninsula

North Side

1 out of top 10 points of interest in this area

While visiting North Side, you might make a stop by sights like Michigan Maritime Museum and North Beach.

Find hotels in North Side

Downtown Hotel Deals

Old Harbor Inn

Old Harbor Inn

3 out of 5
515 Williams Street South Haven MI
The price is ￥23,314 per night from May 21 to May 22
￥23,314
￥25,879 total
May 21 - May 22
includes taxes & fees
9.4/10 Exceptional! (731 reviews)
"Everything great"

Reviewed on May 19, 2026

Old Harbor Inn
Historic Hotel Nichols

Historic Hotel Nichols

2 out of 5
201 Center St South Haven MI
The price is ￥26,731 per night from May 20 to May 21
￥26,731
￥29,671 total
May 20 - May 21
includes taxes & fees
9.8/10 Exceptional! (143 reviews)
"The rooms are always clean and cozy. The staff is top notch and treats all guests like family. Happy hour in the lobby is an amazing way to meet the other guests. We gave stayed twice in room 17 and once in room 10 and look forward to our next stay."

Reviewed on May 17, 2026

Historic Hotel Nichols
Baymont by Wyndham South Haven

Baymont by Wyndham South Haven

2.5 out of 5
1555 Phoenix Rd South Haven MI
Fully refundableReserve now, pay when you stay
The price is ￥13,499 per night from May 31 to Jun 1
￥13,499
￥14,984 total
May 31 - Jun 1
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Convenient location with very reasonable pricing."

Reviewed on May 8, 2026

Baymont by Wyndham South Haven
See all 2,028 properties in Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Downtown

Michigan Maritime Museum

You can spend an afternoon browsing the exhibits at Michigan Maritime Museum in South Haven. While you're in the area, stroll along the beautiful beaches.

Michigan Maritime Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.