Clearing Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jul 29 - Aug 3

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.2/10 - Very good (2,714 reviews)
    "A decent buisness class hotel. No frills. Rooms are smaller, the queen beds are not true queens, and much smaller."
    Reviewed May 22, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    Save 100% on your flight
    €1,670
    €1,016
    per traveller
    found 16 hours ago
    Hotel Felix River North/Magnificent Mile
  • Indoor wedding
    Jul 29 - Aug 3

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,335 reviews)
    "Very good Outstanding service "
    Reviewed May 19, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    €2,088
    €1,072
    per traveller
    found 16 hours ago
    Swissotel - Chicago
  • Terrace/patio
    Jul 29 - Aug 3

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

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (2,504 reviews)
    "I’m not sure if the hotel had a lack of staff but I called for towels and never received any, the next day they brought towels shortly after I called again."
    Reviewed May 21, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    Save 100% on your flight
    €2,197
    €1,315
    per traveller
    found 16 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch, and dinner served
    Jul 29 - Aug 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (3,720 reviews)
    "Fantastic location"
    Reviewed May 22, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    Save 100% on your flight
    €2,214
    €1,359
    per traveller
    found 16 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 29 - Aug 3

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,876 reviews)
    "Excellent"
    Reviewed May 21, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • 1 stop ORD - JFK • 1 stop
    Save 100% on your flight
    €2,250
    €1,436
    per traveller
    found 16 hours ago
    Trump International Hotel & Tower Chicago

Where to stay in Clearing

Find the best Clearing areas and neighborhoods for the activities you enjoy most. Learn more about Clearing
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Clearing

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €137 per night from 25 May to 26 May
€137
25 May - 26 May
includes taxes & fees
8/10 Very Good! (10,129 reviews)
"Could have used a microwave somewhere on property for guests to use. I realized it is an old hotel and the electric probably won't hold up to all room having one. But like one in with the drink machines would be great."

Reviewed on 22 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €187 per night from 27 May to 28 May
€187
27 May - 28 May
includes taxes & fees
9.4/10 Exceptional! (4,210 reviews)
"The hotel was marvelous. The breakfasts were amazing. Anything you could think of was there. The rooftop bar is definitely worth visiting."

Reviewed on 22 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €124 per night from 25 May to 26 May
€124
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,454 reviews)
"Everything was great!"

Reviewed on 22 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,968 properties in Clearing
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.

Frequently asked questions

How much does a Clearing holiday package cost?
Handcraft your Clearing holiday package from an affordable . Pick from any combination of hotels, flights and rental cars to put together the escape you've been dreaming about for ages. Remember to add on one or two experiences!
How do I get a cheap travel package to Clearing?
Bundle your flights and hotels with Expedia to save big on your next getaway. With more than 550 air carriers and 1,000,000 properties globally, your Clearing holiday package can be customized exactly to suit your budget. With all those extra dollars, why not throw in one or more fun experiences and tours? It's an easy way to unlock even more bargains. The holiday you've always dreamed of in Clearing is closer than you thought!
What are the top hotels in Clearing?
Whether you're staying for one or several nights in Clearing, you'll get a wonderful night's rest at Chicago Marriott Midway. This place is popular with lots of travellers.
How far in advance should I book my Clearing holiday?
Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers display prices up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Clearing sometimes occur in the weeks leading up to departure.
What does an Expedia Clearing travel package include?
Hotels, rental cars and flights, or any combination of them — it's up to you! Whether you're exploring Clearing with the entire family or enjoying a solo break, there's a package to match every style and budget. Once you've made your booking, why not add on a few tours and experiences?
What should I know before booking a Clearing travel package?
Our prices are already low. However, you'll enjoy even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Clearing Expedia holiday package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Just select the airline you want and create your ideal Clearing escape.
If I'm not able to travel, can I cancel my Clearing holiday package?
If your travel plans in Clearing have changed, it's good to know that it is possible to cancel or amend your booking. If you booked in the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a fee. For more details, visit our Customer Service Portal.

Popular places to visit

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€38
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€39
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.