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Downtown Chicago Vacation Packages

Downtown Chicago Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Bridgeview/Chicago Area

Super 8 by Wyndham Bridgeview/Chicago Area

2 out of 5
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Bridgeview. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
per person
Jun 5 - Jun 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Hilton Chicago/Oak Brook Suites

Hilton Chicago/Oak Brook Suites

3.5 out of 5
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Villa Park. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Drury Lane Theater and Oakbrook Center Mall are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Chicago Getaway Hostel

Chicago Getaway Hostel

2 out of 5
Lincoln Park
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this hostel in Chicago. Enjoy free breakfast, parking (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Motel 6 Bridgeview, IL

Motel 6 Bridgeview, IL

2 out of 5
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this motel in Bridgeview. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Ridge Shopping Mall and Moraine Valley Community College Fine and Performing Arts Center are located nearby.
Sleep Inn near Great Lakes Naval Base

Sleep Inn near Great Lakes Naval Base

2.5 out of 5
per person
Jun 21 - Jun 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in North Chicago. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Six Flags Great America and Asylum Skate Park are located nearby.
Wingate by Wyndham Tinley Park

Wingate by Wyndham Tinley Park

2.5 out of 5
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this hotel in Tinley Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Odyssey Fun World and Credit Union 1 Amphitheatre are located nearby.

3-4 Night Vacations in Downtown Chicago

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Deerfield/Northbrook

Super 8 by Wyndham Deerfield/Northbrook

2.5 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Bridgeview Inn Chicago Area

Bridgeview Inn Chicago Area

2 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 30 - Jun 3
found 1 day ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)

5-7 Night Vacations in Downtown Chicago

Price found within the past 48 hours. Click for updated prices.
Admiral Motel By Oyo Chicago I-94

Admiral Motel By Oyo Chicago I-94

2.5 out of 5
Chatham
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Cheap Hotel Deals in Downtown Chicago

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Hilton Chicago/Magnificent Mile Suites
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Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
Swissotel - Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Crowne Plaza Chicago West Loop by IHG
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
The Allegro Royal Sonesta Hotel Chicago Loop
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Fairmont Chicago at Millennium Park
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.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Wed, May 14 - Sat, May 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$131 Roundtrip, found 4 days ago
$131
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, May 14 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 24, priced at $131 found 4 days ago
Frontier Airlines
Sat, May 10 - Wed, May 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$210 Roundtrip, found 2 days ago
$210
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, May 10 from Los Angeles Intl. to Midway Intl., returning Wed, May 21, priced at $210 found 2 days ago
American Airlines
Mon, May 12 - Mon, May 19
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$659 Roundtrip, found 5 days ago
$659
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, May 12 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Mon, May 19, priced at $659 found 5 days ago
Swiss International Air Lines
Tue, Jul 1 - Mon, Jul 14
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,154 Roundtrip, found 6 days ago
$1,154
Roundtrip
found 6 days ago
Select Swiss International Air Lines flight, departing Tue, Jul 1 from Pudong Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $1,154 found 6 days ago