Central Chicago Holidays

Photo by Phil Ostroff

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Top Flight + Hotel Deals in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,450, price is now €1,005 per person
€1,005
per person
24 Sept - 29 Sept
found 13 hours ago
Return direct flight included
Vienna (VIE) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The price is really high, and the hotel itself looks nice, but it kinda sucks given the cost.

Reviewed on 11 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €4,696, price is now €3,054 per person
€3,054
per person
17 Sept - 22 Sept
found 1 hour ago
Return direct flight included
Stockholm (ARN) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,064, price is now €1,393 per person
€1,393
per person
24 Sept - 29 Sept
found 13 hours ago
Return direct flight included
Vienna (VIE) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Everything was nice and clean. Staff was very helpful.

Reviewed on 11 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,856, price is now €1,280 per person
€1,280
per person
24 Sept - 29 Sept
found 13 hours ago
Return direct flight included
Vienna (VIE) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on 9 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was €1,782, price is now €1,284 per person
€1,284
per person
24 Sept - 29 Sept
found 13 hours ago
Return direct flight included
Vienna (VIE) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
There were stains on the carpet and where the thermostat was an awful smell coming from that area-like musty smelling. We stayed and paid premium rate for a firework view and while I know they can’t control the weather, I reached out to see if they would be willing to credit something toward a future stay so we could enjoy the experience. Not even an acknowledgment of our disappointment or receipt of our email. Disappointed in the whole situation.

Reviewed on 10 Jul 2026

Where to stay in Central Chicago

Find the best Central Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Central Chicago
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

Find hotels in Magnificent Mile

Top hotels in Central Chicago

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €261 per night from 26 Jul to 27 Jul
€261
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,903 reviews)
"Everything was nice and clean. Staff was very helpful."

Reviewed on 11 Jul 2026

Omni Chicago Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is €160 per night from 27 Jul to 28 Jul
€160
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,733 reviews)
"Check in process was bad, checked in at 6:30 pm and the room was still not ready, i was offered a differed room but it was a downgrade from what i booked, manager didnt offer any Compensation"

Reviewed on 11 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 €197 per night from 10 Aug to 11 Aug
€197
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (10,224 reviews)
"Everything was great!"

Reviewed on 10 Jul 2026

Congress Plaza Hotel
See all 1,356 properties in Central Chicago
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.

Stay near popular Central Chicago attractions

A large stadium surrounded by a cityscape with modern buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Soldier Field

8.8/10 (7,063 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
See properties

What to do in Central Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€21
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€40
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Central Chicago

Frequently asked questions

How much does a Central Chicago holiday package cost?
Go from wondering to wandering with our Central Chicago holiday packages, which start from just €1,005. Pick the flights and hotels that match your travel plans. Then, add on some activities or tours for a one-of-a-kind escape.
How do I get a cheap travel package to Central Chicago?
Browse and lock in everything in one place with our Central Chicago holiday packages. You'll discover bargains on hotels, flights and more that'll keep your travel budget happy and your adventurous spirit full. And, with more than 550 air carriers and 1,000,000 hotels around the globe to choose from, you'll have endless opportunities to mix and match your own way.
Where should I stay in Central Chicago?
A journey to Central Chicago isn't complete without stopping by Wrigley Field and McCormick Place. Stay at a hotel nearby so you can easily access these terrific sights.
What are the top hotels in Central Chicago?
Hilton Garden Inn Chicago Central Loop and Kasa River North Chicago are among the most sought-after properties in Central Chicago. Why not have a look at the rates and facilities at each and then make a decision?
How far in advance should I book my Central Chicago holiday?
Search Expedia to compare international flights as early as possible. You can generally purchase a seat up to a year before departure. If you don't see your preferred carrier, or you've left things to the last moment, don't worry. Cheap fares to Central Chicago sometimes emerge a few weeks before the date of departure.
What does an Expedia Central Chicago travel package include?
Flights, car rentals and hotels — we connect you to the very best deals. All you'll have to do is pick your favourite combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to craft an exciting Central Chicago trip.
What should I know before booking a Central Chicago travel package?
You can save big by bundling your hotels, flights and rental cars. Once you've made your booking, you can add on tours and activities. Your next unforgettable holiday is only a couple of clicks away.
Can I choose my airline with a Central Chicago Expedia holiday package?
With a holiday package, the choice is in your hands. Whether you'd like to fly to Central Chicago in coach or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Central Chicago holiday package?
Because we understand life can be unpredictable, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.

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